Organic EL element

ABSTRACT

Tetraaryldiamie derivatives of formula (1) are used in organic EL elements. ##STR1## R 1 , R 2 , R 3 , and R 4  represent aryl, alkyl, alkoxy, aryloxy, amino or halogen, at least one of R 1  to R 4  is an, aryl group, r1, r2, r3, and r4 are 0 or an integer of 1 to 5, the sum of r1 to r4 is at least 1, R 5  and R 6  represent alkyl, alkoxy, amino or halogen, r5 and r6 are 0 or an integer of 1 to 4. The inventive compounds have high m.p. and high Tg and can be evaporated to deposit tranparent smooth thin films of quality which maintain a stable amorphous state are room temperature over a long term. Organic EL elements using the invertive compound in an organic compound layer, typically a hole injecting and transporting layer thereof provide uniform plane light emission and maintain a high intensity of luminescence in a stable manner over a long term. Thus the elements are fully durable and reliable.

This invention relates to an organic electroluminescent (EL) elementusing an organic compound in the form of a tetraaryldiamine derivative.

BACKGROUND OF THE INVENTION

Low molecular weight organic compound which turn to be conductive orproduce electric charges upon exposure to light, that is, have aphoto-electronic function are well known in the art. Since most of suchcompounds do not possess an ability to form a thin film by themselves,they must be dispersed in or diluted with binder resins and coated ontosubstrates to form thin films. Some compounds have an ability to form athin film by themselves when applied by vacuum deposition. Thesefilm-forming compounds, however, are insufficient in thin film stabilityand liable to physical changes, typically phase transition.

Specific tetraaryldiamines are disclosed in Japanese Patent ApplicationKokai (JP-A) No. 277071/1990 as a material for forming a photosensitivelayer on an electrophotographic photoconductor. Their potential use asan organic EL element-forming compound is suggested nowhere.

Organic electroluminescent (EL) elements include a thin film containinga luminescent organic compound interleaved between a cathode and anCode. Electrons and holes are injected into the thin film where they arerecombined to create excitons. Light is emitted by utilizingluminescence (phosphorescence or fluorescence) upon deactivation ofExcitons. The organic EL elements are characterized by plane lightemission at a high luminance of about 100 to 100,000 cd/m² with a lowvoltage of about 10 volts and light emission in a spectrum from blue tored color by a simple choice of the type of fluorescent material.

The organic EL elements, however, are undesirably short an effectivelife, less durable and less reliable because of the following factors.

(1) Physical changes of organic compounds: Development and growth ofgrain boundaries render the interface non-uniform, which causesdeterioration of electric charge injecting ability, short-circuiting anddielectric breakdown of the element. Particularly when a low molecularweight compound having a molecular weight of less than 500 is used,grain boundaries develop and grow, substantially detracting from filmquality. Even when the interface with indium tin oxide (ITO) is rough,significant development and growth of grain boundaries occur to lowerluminous efficiency and allow current leakage, ceasing to emit light.Local dark spots are also formed.

(2) Oxidation and stripping of the cathode: Although metals having a lowwork function such as Mg, Li, Na, and Al are used as the cathode inorder to facilitate electron injection, these metals are reactive withoxygen and moisture in air. As a result, the cathode can be strippedfrom the organic compound layer, prohibiting electric charge injection.Particularly when a polymeric compound is applied by a wet process suchas spin coating, the residual solvent and decomposed products resultingfrom film formation promote oxidative reaction of the electrodes whichcan be stripped to create local dark spots.

(3) Low luminous efficiency and increased heat build-up: Since electriccurrent is conducted across an organic compound, the organic compound isplaced under an electric field of high strength and cannot help heating.The heat causes melting, crystallization or decomposition of the organiccompound, leading to deterioration or failure of the element.

(4) Photo-chemical and electrochemical changes of organic compoundlayers.

One solution to these problems is an organic EL device comprising a holeinjecting and transporting zone including a hole injecting porphyriniccompound and a hole transporting aromatic tertiary amine as disclosed inVanSlyke at al. U.S. Pat. No. 4,120,432 or JP-A 295695/1988. Moreparticularly, the EL devices prepared in Examples 1, 10 and 11 include atransparent anode of indium tin oxide coated glass, a hole injectingcopper phthalocyanine PC-10 layer (35 nm or 37.5 nm), a holetransporting 1,11'-bis(4-di-p-tolylaminophenyl)cyclohexane ATA-1 layer(35 nm or 37.5 nm), a light emitting and electron injecting andtransporting aluminum trisoxine CO-1 layer (60 nm), and a Mg-Ag cathode(200 nm). When these devices were driven for 500 hours at a constantcurrent density of 5 mA/cm², the light output declined from 0.08 mW/cm²at the initial to 0.05 mW/cm² at the final (percentage decline 37.5%).At a current density of 20 mA/cm², the light output declined from 0.45mW/cm² at the initial to 0.06 mW/cm² at the final (percentage decline86.7%). At a current density of 40 mA/cm², the light output declinedfrom 1.15 mW/cm² at the initial to <0.1 mW/cm² at the final (percentagedecline >91.3%). The other hole transporting aromatic tertiary aminesused in Examples 12 and 13 areN,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl (ATA-7) andN,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl (ATA-8) which are bothdeposited to a thickness of 37.5 nm. As compared with ATA-1, ATA-7showed lower initial outputs at the same current density and ATA-7 andATA-8 showed an output decline of 62.5% and 60%, respectively.

A combination of a triarylamine (ATA-1) and a tetra-arylamine (ATA-7) isdescribed in Example 14 and 15. This provides a low initial output atthe same current density and a considerable output decline. As seen fromthese results, the life of these light-emitting elements is yet belowthe practically acceptable level. Particularly when the elements aredriven with a high current density for the purpose of producing light ofa high output or luminance clearing the practically acceptable level, adrastic output drop occurs during nearly initial operation.

For the purpose of improving such a drastic output drop, specific holetransporting aromatic tertiary amines are useful as disclosed inVanSlyke et al. U.S. Pat. No. 5,061,569 or JP-A 234681/1993. Moreparticularly, the aromatic tertiary amine is comprised of at least twotertiary amine moieties and includes attached to a tertiary aminenitrogen atom an aromatic moiety having at least two fused aromaticrings. Use of these specific hole transporting aromatic tertiary amines,however, leaves it still difficult to achieve stable light emission overa long time. The light-emitting elements have a lifetime yet below thepractically acceptable level.

This is because the hole transporting aromatic tertiary amines are lessresistant against heat. By heat generation due to the Joule heat of anelement, an amorphous thin film can become unstable. An organic ELelement using such a thin film has low luminous efficiency and a shortlight-emitting life and remains less durable and less reliable.

The transparent electrodes used heretofore are of ITO-on-glass or thelike because they must have a low surface resistivity of less than 10 to30 Ω/cm². However, observation under a scanning tunnel microscope (STM)or atomic force microscope (AFM) indicates irregularities of the orderof 20 nm on sputtered film-bearing substrates and of the order of 40 nmon EB evaporated film-bearing substrates. There is also surfaceroughening due to damage during ITO patterning. Therefore, theprevailing situation is likely to promote crystallization of an organicthin film.

Solutions in this respect include provision of a metal-containing ormetal-free phthalocyanine film on the ITO surface (see theabove-referred U.S. Pat. No. 4,720,432 or JP-A 295695/1988) and spincoating of polyarylene vinylene. However, the phthalocyanine whether ornot it contains a metal is microcrystalline and is not always effective.The polyarylene vinylene can damage ITO with an acid generated uponconversion and promote oxidation of the electrodes by residual solventor the like. A film of polyarylene vinylene is non-uniform because ofspin coating. All these fail to improve element reliability.

For the purpose of improving element performance, EL elements having amix layer consisting of a mixture of two or more compounds havingdistinct functions were also proposed. For example, JP-A 250292/1990discloses that a thin film of layered structure or a mix thin filmprepared from an organic compound having hole transporting and lightemitting functions and another organic compound having an electrontransporting function is used as a light emitting layer for the purposeof improving luminance and durability. JP-A 291696/1990 discloses to usea thin film of a mixture of an organic compound having a holetransporting function and a fluorescent organic compound having anelectron transporting function as a light emitting layer. JP-A114197/1991 discloses to interpose a mix layer of a mixture of anelectric charge injecting material and an organic fluorescent materialbetween an electric charge injecting layer and a light emitting layerfor the purpose of improving luminous efficiency and luminance. JP-A190089/1991 discloses to interpose between a hole transporting layerand/or an electron transporting layer and an organic light emittinglayer a mix layer containing the components of the opposed layers forthe purpose of facilitating injection of holes and electrons into thelight emitting layer. JP-A 334894/1992 discloses that when a pluralityof organic compound layers are formed, a layer in which compounds ofdistinct functions are co-present is formed, for example, a layercontaining a hole transporting luminescent material and an electrontransporting material is formed, thereby increasing luminance, providinga variety of emission color hues and improving durability. JP-A182762/1993 discloses to form a mix layer of a mixture of a luminescentmaterial a an electric charge injecting material between a lightemitting layer and an electric charge injecting layer, thereby loweringthe drive voltage. JP-A 289090/1991 discloses to form a thin film of amixture of a hole conducting organic compound and an organic complex ofa rare earth metal as a light emitting layer, achieving a narrowluminous spectrum, monochromaticity, and high conversion efficiency.JP-A 178487/1992 and 78655/1993 discloses high luminance full-colorelements which are obtained by forming a thin film layer of a mixture ofan organic charge material and an organic luminescent material as anorganic luminescent thin film layer, thereby preventing concentrationextinction and increasing the available range of luminescent material.Moreover, JP-A 357694/1992 discloses to for layers of graded structurein which a concentration gradient is provided between adjacent layers bycomponents of respective layers, thereby lowering the drive voltage andimproving durability.

Also organic compound layers doped with rubrene were proposed. Typicalexamples of known organic compound layers doped with rubrene are foundin organic EL elements comprising a hole transporting layer in the formof a film of a mixture of hydrazine derivatives and a light emittinglayer of tris(8-quinolinolato)aluminum as organic compound layerswherein the hole transporting layer is doped with rubrene or a halfportion of the hole transporting layer disposed on the organic interfaceand the entire light emitting layer are doped with rubrene. It wasreported that in the element having the hole transporting layer dopedwith rubrene, light emission takes place from bothtris(8-quinolinolato)aluminum and rubrene and that in the element havinga half portion of the hole transporting layer and the light emittinglayer doped with rubrene, luminous efficiency is improved and theincrease of dark spots during shelf storage is suppressed. See Kanai,Yajima & Sato, Extended Abstracts of the 39th Spring Meeting, 1992 ofThe Japan Society of Applied Physics and Related Societies,28p-Q-8(1992) and Sato & Kanai, Preprint of Workshop 92 of the JapaneseResearch Association for Organic Electronics Materials (JOEM), 31(1992). A hole transporting layer of triphenyldiamnie derivative (TPD)doped with rubrene was also proposed as having an improved luminancehalf-life. See Fujii, Sano, Fujita, Hamada & Shibata, Extended Abstractsof the 54th Autumn Meeting, 1993 of The Japan Society of AppliedPhysics, 29p-ZC-7 (1993).

Moreover, JP-A 207488/1990 discloses an element comprising a p-typeinorganic semiconductor thin film layer and an organic compound thinfilm layer consisting essentially of rubrene, the element providingsatisfactory luminance and stability thereof.

None of the foregoing EL elements are satisfactory in luminous life.

SUMMARY OF THE INVENTION

A primary object of the present invention is to provide an organic ELelement using an organic compound in the form of a tetrolyldiaminederivative which ban a high melting point and high glass transitiontemperature and thus improved thermal properties, allows a thin filmthereof to remain stable in an amorphous state over a long term, canform a thin film by itself without a need for a binder resin,experiences minimal physical, photo-chemical and electro-chemicalchanges, and has a photo-electron function.

Another object of the present invention is to provide a durable,reliable, high luiinance organic EL element having an etende emissionlife by using the specific compound.

A furter object of the present invention is to provide a highreliability, high luminance light emitting element featuring minimizedvoltage rise, current leakage, and delopmnet or growth of local darkspots during driving of the element as well as a minimized initial dropof luminance.

According to the invention, there is provided an organicelectroluiminescent (EL) element or device comprising at least one layercontaining at least one organic electro-luminescent element-formingcompound which is a tetra-aryldiamire derivative of the followingformula (1). ##STR2##

R₁, R₂, R₃, and R₄ are independently select from the group consisting ofan aryl group, alkyl group, alkoxy group, aryloxy group, amino group andhalogen atom, at least one of R₁, R₂, R₃, and R₄ is an aryl group; r1,r2, r3, and r4 are independently 0 or an integer of 1 to 5, the sum ofr1, r2, r3, and r4 is an integer of at least 1; R₅ and R₆ areindependently selected from the group consisting of an alkyl group,alkoxy group, amino group, and halogen atom; and r5 and r6 areindependently 0 or an integer of 1 to 4.

Preferably, two to four of R₁ to R₄ are aryl groups, at least two of thearyl groups are attached to the corresponding benzene ring at the para-or meta-position with respect to the position of attachment to thenitrogen atom. Preferably, at least one of the aryl groups representedby R₁ to R₄ is phenyl. Preferably at least one of the aryl groupsrepresented by R₁ to R₄ is a naphthyl, anthryl, pyrenyl, perylenyl orcoronenyl group.

In one preferred embodiment, the compound has the following formula (2).##STR3##

A₁, A₂, A₃, and A₄, which may be identical or different, are phenylgroups attached to the corresponding benzene ring at the para- ormeta-position with respect to the position of attachment to the nitrogenatom; R₇, R₈, R₉, and R₁₀ are independently selected from the groupconsisting of an alkyl group, alkoxy group, aryl group, aryloxy group,amino group and halogen atom; r7, r8, r9, and r10 are independently 0 oran integer of 1 to 4; R₅ and R₆ are independently selected from thegroup consisting of an alkyl group, alkoxy group, amino group, andhalogen atom; and r5 and r6 are independently 0 or an integer of 1 to 4.

In another preferred embodiment, the compound has the following formula(3). ##STR4##

Ar is an aryl group attached to the corresponding benzene ring at thepara- or meta-position with respect to the position of attachment tothe-nitrogen atom; Z₁, Z₂, and Z₃ are independently selected from thegroup consisting of an alkyl group, alkoxy group, aryl group, aryloxygroup, amino group and halogen atom, at least one of Z₁, Z₂, and Z₃ isan aryl group attached to the corresponding benzene ring at the para- ormeta-position with respect to the position of attachment to the nitrogenatom, with the proviso that all of Ar, Z₁, Z₂, and Z₃ are not phenylgroups each attached to the corresponding benzene ring at the para- ormeta-position with respect to the position of attachment to the nitrogenatom at the same time; s1, s2, and s3 are independently 0 or an integerof 1 to 5, the sum of s1, s2 and s3 is an integer of at least 1; R₀ isselected from the group consisting of an alkyl group, alkoxy group, arylgroup, aryloxy group, amino group and halogen atom; r₀ is 0 or aninteger of 1 to 4; R₅ and R₆ are independently selected from the groupconsisting of an alkyl group, alkoxy group, amino group, and halogenatom; and r5 and r6 are independently 0 or an integer of 1 to 4.

In a further preferred embodiment, the compound has the followingformula (4). ##STR5##

R₇, R₈, R₉, and R₁₀ are independently selected from the group consistingof an alkyl group, alkoxy group, aryl group, aryloxy group, amino groupand halogen atom; r7, r8, r9, and r10 are independently 0 or an integerof 1 to 4; R₁₁, R₁₂, R₁₃, and R₁₄ are independently selected from thegroup consisting of an alkyl group, alkoxy group, aryl group, aryloxygroup, amino group and halogen atom; r11, r12, r13, and r14 areindependently 0 or an integer of 1 to 5; R₅ and R₆ are independentlyselected from the group Consisting of an alkyl group, alkoxy group,amino group, and halogen atom; and r5 and r6 are independently 0 or aninteger of 1 to 4. More preferably r5, r6, r7, r8, r9, r10, r11, r12,r13, and r14 are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (5). ##STR6##

R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, r 5, r6, r7, r8, r9, r10,r11, r12, r13, and r14 are as defined above. More preferably, r5, r6,r7, r8, r9, r10, r11, r12, r13, and r14 are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (6): ##STR7##

R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, r5, r6, r7, r8, r9, r10,r11, r12, r13, and r14 are as defined above. More preferably, r5, r6,r7, r8, r9, r10, r11, r12, r13, and r14 are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (7): ##STR8##

R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, r5, r6, r7, r8, r9, r10,r11, r12, r13, and r14 are as defined above. More preferably, r5, r6,r7, r8, r9, r10, r11, r12, r13, and r14 are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (8). ##STR9##

R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, r5, r6, r7, r8, r9, r10,r11, r12, r13, and r14 are as defined above. More preferably, r5, r6,r7, r8, r9, r10, r11, r12, r13, and r14 are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (9). ##STR10##

R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁,R₁₂, R₁₃, R₁₄, r5, r6, r7, r8, r9, r10,r11, r12, r13, and r14 are as defined above. More preferably, r5, r6,r7, r8, r9, r10, r11, r12, r13, and r14 are equal to 0.

In a still further preferred enbodiment, the compound has the followingformula (10). ##STR11##

Ar₁ and Ar₂ which may be identical or different are aryl groups; R₁₅ andR₁₆ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryl group, aryloxy group, amino group and halogenatom; r15 and r16 are independently 0 or an integer of 1 to 4; R₁₇ andR₁₈ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryloxy group, amino group and halogen atom; r17and r18 are independently 0 or an integer of 1 to 5; R₅ and R₆ areindependently selected from the group consisting of an alkyl group,alkoxy group, amino group, and halogen atom; and r5 and r6 areindependently 0 or an integer of 1 to 4. More preferably, r5, r6, r15,r16, r17, and r18 are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (11). ##STR12##

Ar₁ and Ar₃ which may be identical or different are aryl groups; R₁₅ andR₂₀ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryl group, aryloxy group, amino group and halogenatom; r15 and r20 are independently 0 or an integer of 1 to 4; R₁₈ and R₁₉ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryloxy group, amino group and halogen atom; r18and r19 are independently 0 or an integer of 1 to 5; and R₅, R₆, r5 andr6 are as defined above. More preferably, r5, r6, r15, r18, r19, and r20are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (12). ##STR13##

Ar₁, Ar₂, and Ar₃ which may be identical or different are aryl groups;R₁₅, R₁₆, and R₂₀ are independently selected from the group consistingof an alkyl group, alkoxy group, aryl group, aryloxy group, amino groupand halogen atom; r15r16and r20 are independently 0 or an integer of 1to 4; R₁₈ is selected from the group consisting of an alkyl group,alkoxy group, aryloxy group, amino group and halogen atom; r18 is 0 oran integer of 1 to 5; and R₅, R₆, r5 and r6 are as defined above. Morepreferably, r5, r6, r15, r16, r18, and r20 are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (13). ##STR14##

Ar₄ and Ar₅ which may be identical or different are aryl groups; R₁₅ andR₁₆ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryl group, aryloxy group, amino group and halogenatom; r15 and r16 are independently 0 or an integer of 1 to 4; R₁₇ andR₁₈ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryloxy group, amino group and halogen atom; r17and r18 are independently 0 or an integer of 1 to 5; and R₅, R₆, r5 andr6 are as defined above. More preferably, r5, r6, r15, r16, r17, and r18are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (14). ##STR15##

Ar₄ and Ar₆ which may be identical or different are aryl groups; R₁₅ andR₂₀ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryl group, aryloxy group, amino group and halogenatom; r15 and r20 are independently 0 or an integer of 1 to 4; R₁₈ andR₁₉ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryloxy group, amino group and halogen atom; r18and r19 are independently 0 or an integer of 1 to 5; and R₅, R₆, r5 andr6 are as defined above. More preferably, r5, r6, r15, r18, r19, and r20are equal to 0.

In a still further preferred embodiment, the compound has the followingformula (15). ##STR16##

Ar₄, Ar₅, and Ar₆ which may be identical or different are aryl groups;R₁₅, R₁₆, and R₂₀ are independently selected from the group consistingof an alkyl group, alkoxy group, aryl group, aryloxy group, amino groupand halogen atom; r15, r16, and r20 are independently 0 or an integer of1 to 4; R₁₈ is selected from the group consisting of an alkyl group,alkoxy group, aryloxy group, amino group and halogen atom; r18 is 0 oran integer of 1 to 5; and R₅, R₆, r5 and r6 are as defined above. Morepreferably, r5, r6, r15, r16, r18, and r20 are equal to 0.

Preferably the organic EL element includes at least one mix layercontaining a mixture of at least one organic EL element-forming compoundas defined above and at least one compound having an electron injectingand transporting function. Preferably, the compound having an electroninjecting and transporting function is tris(8-quinolinolato)aluminum.Preferably, the mix layer is a light emitting layer.

Preferably, at least one layer containing at least one organic ELelement-forming compound is doped with a fluorescent material, typicallyrubrene.

Preferably, the layer containing at least one organic EL element-formingcompound is a hole injecting and transporting layer and the elementfurther includes a light emitting layer. The hole injecting andtransporting layer preferably includes at least two layers havingdifferent compositions. Preferably at least one of the hole injectingand transporting layers contains a polythiophene.

Also preferably, the organic EL element further includes an electroninjecting and transporting layer.

Further preferably, the layer containing at least one organicelectroluminescent element-forming compound is a layer having a holeinjecting and transporting function; a layer having a light emittingfunction or electron injecting and transporting function is disposedadjacent the layer; and the difference in ionization potential Ipbetween the layer having a hole injecting and transporting function andthe layer having a light emitting function or electron injecting andtransporting function is at least 0.25 eV.

BENEFITS OF THE INVENTION

The compounds for use in organic EL elements according to the inventionare tetraaryldiamine derivatives of formula (1) having a high meltingpoint and a high glass transition temperature (Tg). Thin films formedfrom these compounds as by evaporation are of quality in that they aretransparent, keep a stable amorphous state at room temperature orhigher, and maintain a smooth surface film of quality over an extendedperiod of time. Therefore, the compounds can be formed into thin filmsby themselves without a need for binder resins.

These advantages are derived from the following facts. 1) The compoundis increased in molecular weight so as to have a higher melting point.2) A bulky substituent providing steric hindrance such as a phenyl groupis introduced to optimize intermolecular overlap. 3) The number ofconformations that the molecule can assume is increased to restrainrearrangement of the molecule.

Further due to inclusion of many hole injecting and transporting unitssuch as N-phemyl groups and introduction of phenyl groups in R₁ to R₄ toform biphenyl groups, there is available an expanded π-conjugated systemwhich is advantageous for carrier transportation. This results in asignificantly improved hole injecting and transporting capability.

Since the organic EL element of the invention uses a tetraaryldiaminederivative of formula (1) as an organic EL element-forming compound inan organic compound layer, typically a hole injecting and transportinglayer, the element ensures uniform plane light emission and maintainshigh luminance over a long period of time in a stable manner. Theelement maintains emission at a high luminance of about 100 to 100,000cd/m² or even higher over a long period of time in a stable mannerthough the luminance depends on the wavelength of emitted radiation. Itis to be noted that the organic EL elements of the invention emit lightat a maximum wavelength in the range of about 350 to 700 nm. Heatresistance and durability are high enough to allow for stable operationof the element even at a current density as high as about 1 A/cm² ormore.

In an embodiment wherein the inventive compound is used in an organiccompound layer of an organic EL element, the energy level is optimizedand carriers are effectively blocked at the interface, ensuring stablecarrier recombination and light emission. Especially when the inventivecompound is used in a hole injecting and transporting layer of anorganic EL element, the difference in ionization potential Ip betweenthe hole injecting and transporting layer and a layer disposed adjacentthereto and having a light emitting or luminescent function (inclusiveof a light emitting layer also serving as an electron injecting andtransporting layer, that is, light emitting/electron injecting andtransporting layer) or between the hole injecting and transporting layerand an electron injecting and transporting layer disposed adjacentthereto (where the hole injecting and transporting layer is a layerhaving a hole injecting and transporting function and also serving as alight emitting layer) is optimized. Then the carrier blocking effect atthe interface is enhanced and injection of polarly inferior or unstablecarriers is less probable. The organic compounds in the respectivelayers are less susceptible to damage and few points of deactivation ofcarriers or excitons are created in the carrier recombination region orlight emitting region. This results in stable light emission and asignificantly extended life.

In an embodiment wherein an organic compound layer containing a mixtureof the inventive compound and a compound having an electron injectingand transporting function is provided, typically as a light emittinglayer, carrier hopping conduction paths are created in the mix layer,allowing carriers injected into the mix layer to move through a polarlypredominant material. More particularly, holes move through a holeinjecting and transporting material and electrons move through anelectron injecting and transporting material while injection of carriersof opposite polarity is rather inhibited. The respective organiccompounds are less susceptible to damage. As a result, the EL elementhas a substantially extended life.

In an embodiment wherein an organic compound layer containing theinventive compound is doped with a fluorescent material, by using theinventive compound in a hole injecting and transporting layer of anorganic EL element, the difference in ionization potential Ip betweenthe hole injecting and transporting layer and a layer disposed adjacentthereto and having a light emitting function (inclusive of a lightemitting layer also serving as an electron injecting and transportinglayer, that is, light emitting/electron injecting and transportinglayer) or between the hole injecting and transporting layer and anelectron injecting and transporting layer disposed adjacent thereto(where the hole injecting and transporting layer is a layer having ahole injecting and transporting function and also serving as a lightemitting layer) is optimized. Then the carrier blocking effect at theinterface is enhanced and injection of polarly inferior or unstablecarriers is less probable. The organic compounds in the respectivelayers are less susceptible to damage and few points of deactivation ofcarriers or excitons are created in the carrier recombination region orlight emitting region. Where the organic compound layer is additionallydoped with a fluorescent material in the form of rubrene, which has abipolar transporting ability and allows for carrier recombination, thedamage to the organic compound is accordingly reduced. Further, sincerubrene is present in proximity to the carrier recombination region,energy transfer from excitons to rubrene takes place to reducenon-radiative deactivation, resulting in stable light emission and asignificantly extended life.

BRIEF DESCRIPTION OF THE DRAWINGS

The foregoing aspects and other features of the invention are explainedin the following description, taken in connection with the accompanyingdrawings where:

FIG. 1 is a side elevation of an exemplary organic EL element accordingto one embodiment of the invention.

FIG. 2 is a block diagram showing a low energy electron spectrometersystem.

FIG. 3 is a graph showing a photoelectron yield as a function ofexcitation energy.

FIG. 4 is a diagram showing a IR absorption spectrum of the inventivecompound (I-1) of Example 1.

FIG. 5 is a diagram showing a NMR spectrum of compound (I-1).

FIG. 6 is a diagram showing a IR absorption spectrum of the inventivecompound (II-1) of Example 2.

FIG. 7 is a diagram showing a NMR spectrum of compound (II-1).

FIG. 8 is a diagram showing a IR absorption spectrum of the inventivecompound (VII-1) of Example 3.

FIG. 9 is a diagram showing a NMR spectrum of compound (VII-1).

FIG. 10 is a diagram showing a IR absorption spectrum of the inventivecompound (X-10) of Example 4.

FIG. 11 is a diagram showing a NMR spectrum of compound (X-10).

DETAILED DESCRIPTION TO THE INVENTION

The compound for use in an organic EL element according to theinvention, which is often referred to as "inventive compound" throughoutthe specification, is a tetraaryldiamine derivative of formula (1).##STR17##

In a formula (1), R₁, R₂, R₃, and R₄ independently represent an arylgroup, alkyl group, alkoxy group, aryloxy group, amino group or halogenatom. They may be identical or different. At least one of R₁, R₂, R₃,and R₄ groups is an aryl group. Letters r1, r2, r3, and r4 areindependently 0 or an integer of 1 to 5. All of r1, r2, r3, and r4 arenot equal to 0 at the same time, therefore, the sum of r1+ r2+r3+r4 isan integer of 1 or more which satisfies the requirement that at leastone aryl group is present. R₅ and R₆ independently represent an alkylgroup, alkoxy group, amino group or halogen atom. They may be identicalor different. Letters r5 and r6 are independently 0 or an integer of 1to 4.

The aryl group represented by R₁ to R₄ may be either monocyclic orpolycyclic and inclusive of a fused ring and gathered rings. The arylgroup preferably has 6 to 20 carbon atoms in total and may have asubstituent. Exemplary substituents are alkyl, alkoxy, aryl, aryloxy,amino groups, and halogen atoms. Illustrative examples of the aryl grouprepresented by R₁ to R₄ include phenyl, o-, m- and p-tolyl, pyrenyl,naphthyl, anthryl, biphenyl, phenylanthryl, and tolylanthryl groups,with the phenyl group being preferred. The aryl group, especially phenylgroup is preferably attached to the 3- or 4-position (meta- orpara-position) of the benzene ring with respect to the position ofattachment to the nitrogen atom.

The alkyl group represented by R₁ to R₄ may be either normal orbranched. The alkyl group preferably has 1 to 10 carbon atoms and mayhave a substituent. Exemplary substituents are the same as describedabove in conjunction with the aryl group. Illustrative examples of thealkyl group represented by R₁ to R₄ include methyl, ethyl, n- andi-propyl, and n-, i-, s- and t-butyl groups.

The alkoxy group represented by R₁ to R₄ is preferably one in which thealkyl moiety has 1 to 6 carbon atoms. It may have a substituent.Illustrative examples of the alkoxy group represented by R₁ to R₄include methoxy, ethoxy, and t-butoxy groups.

Examples of the aryloxy group represented by R₁ to R₄ include phenoxy,4-methylphenoxy, and 4-(t-butyl)phenoxy groups

The amino group represented by R₁ to R₄ may be either substituted orunsubstituted, preferably substituted. Exemplary are dimethylamino,diethylamino, diphenylamino, bis(biphenyl)amino, N-phenyl-N-tolylamino,N-phenyl-N-biphenylamino, bis(naphthylamino), bis(anthryl)amino, andbis(pyrenyl)amino groups.

Exemplary of the halogen atom represented by R₁ to R₄ are chlorine andbromine atoms.

At least one of R₁ to R₄ is an aryl group. Preferably two to four arylgroups are present in a molecule as R₁ to R₄, and two to four of r1 tor4 age preferably integers of at least 1. Further preferably, two tofour aryl groups in total are present in a molecule, more preferably twoto four of r1 to r4 are equal to 1, especially r1 to r4 being equalto 1. Most preferably all of R₁ to R₄ included are aryl groups. Moreparticularly, on the four benzene rings which may have R₁ to R₄substituents in a molecule, there may be present two to four aryl groupsin total. The benzene ring to which two to four aryl groups are attachedmay be identical or different among the four benzene rings although itis preferred that two to four aryl groups are individually attached todifferent benzene rings. It is more preferred that at least two arylgroups are attached to the corresponding benzene rings at their para- ormeta-position with respect to the position of attachment to the nitrogenatom. It is preferred that among the aryl groups, at least one is aphenyl group, that is, an aryl group and the benzene ring, takentogether, form a 4- or 3-biphenylyl group with respect to the nitrogenatom. Especially, two to four 4- or 3-biphenylyl groups are included. Inthis case, either one or both of 4- and 3-biphenylyl groups may bepresent. Preferred aryl groups other than phenyl include 1-or2-naphthyl, 1-, 2- or 9-anthryl, pyrenyl, perylenyl, and coronenylgroups. Also preferably, aryl groups other than phenyl are attached tothe corresponding benzene rings at their para- or meta-position withrespect to the position of attachment to the nitrogen atom. A mixture ofphenyl and other aryl groups is also acceptable.

In formula (1), R₅ and R₆ represent an alkyl group, alkoxy group, aminogroup or halogen atom, examples of which are the same as described forR₁ to R₄. Although letters r5 and r6 are independently 0 or an integerof 1 to 4, it is preferred that both r5 and r6 be equal to 0. It ispreferred that the biphenylene group connecting the two arylamino groupsbe unsubstituted.

Where r1 to r4 are integers of at least 2, the groups represented byeach of R₁ to R₄ may be identical or different. Similarly, where r5 andr6 are integers of at least 2, the groups represented by each of R₅ andR₆ may be identical or different.

Preferred among the compound of formula (1) are compounds of formulae(2) and (3). ##STR18##

Formula (2) is first described. In formula (2), A₁, A₂, A₃, and A₄,which may be identical or different, are phenyl groups attached to thecorresponding benzene rings at their para- or meta-position (4- or3-position) with respect to the position of attachment to the nitrogenatom. These phenyl groups may be substituted or unsubstituted, with thepreferred substituents being the same as described for the aryl grouprepresented by R₁ to R₄.

R₇ to R₁₀ independently represent an alkyl group, alkoxy group, arylgroup, aryloxy group, amino group or halogen atom, they may be identicalor different. Illustrative examples of these groups are the same asdescribed for R₁ to R₄ of formula (1).

Letters r7 to r10 are independently 0 or an integer of 1 to 4.Preferably r7 to r10 are equal to 0.

R₅, R₆, r5 and r6 are as defined for formula (1), with r5=r6=0 beingpreferred.

Where r7 to r10 are integers of at least 2, the groups represented byeach of R₇ to R10 may be identical or different.

Next formula (3) is described. In formula (3), Ar is an aryl groupattached to the corresponding benzene ring at its para- or meta-positionwith respect to the position of attachment to the nitrogen atom.Exemplary aryl groups are the same as the aryl group represented by R₁to R₄ in formula (1). The aryl group may be substituted orunsubstituted, with the preferred substituents being the same asdescribed for the aryl group represented by R₁ to R₄. An amino group isa preferred substituent. It is noted that the amino group may becyclized to form a heterocyclic ring. Exemplary amino groups are thoseamino groups described in conjunction with R₁ to R₄.

Z₁, Z₂, and Z₃ independently represent an alkyl group, alkoxy group,aryl group, aryloxy group, amino group or halogen atom. Examples ofthese groups are the same as previously described in conjunction with R₁to R₄ in formula (1). At least one of Z₁, Z₂, and Z₃ is an aryl groupattached to the corresponding benzene ring at the para- or meta-positionwith respect to the position of attachment to the nitrogen atom. It isto be noted that, all of Ar, Z₁, Z₂, and Z₃ are not phenyl groups eachattached to the corresponding benzene ring at the para- or meta-positionwith respect to the position of attachment to the nitrogen atom at thesame time. It is preferred that two to three of the four benzene ringseach have an aryl group at the para-or meta-position. It is thuspreferred that one or two of Z₁ to Z₃ groups are such aryl groups.Preferred aryl groups include 1- and 2-naphthyl, 1-, 2- and 9-anthryl,pyrenyl, perylenyl and coronenyl groups, with phenyl being mostpreferred. The aryl groups represented by Z₁ to Z₃ may be substitute orunsubstituted, with the preferred substituents being the same asdescribed for the aryl group represented by R₁ to R₄. An amino group isa preferred substituent. Exemplary amino groups are those amino groupsdescribed in conjunction with R₁ to R₄.

Letters s1, s2, and s3 are independently 0 or an integer of 1 to 5. Theyare not equal to 0 at the same time, that is, the sum of s1, s2 and s3is an integer of at least 1. Preferably s1, to s3 are respectively 0 or1, more preferably one or two of s₁ to 63 are equal to 1 and theremainings are 0. Z₁ to z₃ included when s1 to s3 are equal to 1 arepreferably aryl groups, especially phenyl groups attached to thecorresponding benzene rings at their para- or meta-position with respectto the position of attachment to the nitrogen atom. Where s1 to s3 informula (3) are integers of at least 2, the respective Z₁, to Z₃ groupsmay be identical or different.

In formula (3), R₀ and r0 are as defined for R₇ and r7 in formula (2),respectively. R₅, R₆, r5 and r6 are as defined in formula (2), withtheir preferred examples and ranges being also the same.

Most preferred among the compound of formula (2) are compounds offormulae (4) to (9). ##STR19##

In these formulae, R₁₁ to R₁₄ independently represent an alkyl group,alkoxy group, aryl group, aryloxy group, amino group or halogen atom.They may be identical or different. Illustrative examples of thesegroups are the same as described for R₁ to R₄ of formula (1)

Letters r11 to r14 are independently 0 or an integer of 1 to 5. It ispreferred in all formulae (4) to (9) that r11 to r14 be equal to 0.Where r11 to r14 are integers of at least 2, the groups represented byeach of R₁₁ to R₁₄ may be identical or different.

In formulae (4) to (9), R₅ to R₁₀ and r5 to r10 are as defined informula (2), with their preferred examples And ranges being also thesame.

Most preferred among the compound of formula (3) are compounds offormulae (10) to (15). ##STR20## In these formulae, Ar₁ to Ar₆ are arylgroups. Ar₁ and Ar₂ in formula (10), Ar₁ and Ar₃ in formula (11), Ar₁,Ar₂ and Ar₃ in formula (12), Ar₄ and Ar₅ in formula (13), Ar₄ and Ar₆ informula (14), and Ar₄, Ar5 and Ar₆ in formula (15) may be identical ordifferent. Illustrative examples of the aryl group are the same asdescribed for R₁ to R₄ of formula (1), with the phenyl group beingespecially preferred.

R₁₅ in formulae (10) to (15), R₁₆ in formulae (10), (12),. (13) and(15), and R₂₀ in formulae (11), (12), (14) and (15) independentlyrepresent an alkyl group, alkoxy group, aryl group, aryloxy group, aminogroup or halogen atom. R₁₅ and R₁₆ in formula (10) or (13), R₁₅ and R₂₀in formula (11) or (14), and R₁₅, R16 and R₂₀ in formula (12) or (15)may be identical or different. Illustrative examples of these groups arethe same as described for R₁ to R₄ of formula (1).

Letters r15 in formulae (10) to (15), r16 in formulae (10), (12), (13)and (15), and r20 in formulae (11), (12), (14) and (15) areindependently 0 or an integer of 1 to 4, with r15=r16=r20=0 beingpreferred.

R₁₇ in formulae (10) and (13), R₁₈ in formulae (10) to (15), and R₁₉ informulae (11) and (14) independently represent an alkyl group, alkoxygroup, aryloxy group, amino group or halogen atom. R₁₇ and R₁₈ informula (10) or (13) and R18 and R19 in formula (11) or (14) may beidentical or different. Illustrative examples of these groups are thesame as described for R₁ to R₄ of formula (1).

Letters r17 in formulae (10) and (13), r18 in formulae (10) to (15), andr19 in formulae (11) and (14) are independently 0 or an integer of 1 to5, with r17=r18 =r19=0 being preferred.

In formulae (10) to (15), where r15, r16 and r20 are integers of atleast 2, the groups represented by each of R₁₅, R₁₆ and R₂₀ may beidentical or different and where r17, r18 and r19 are integers of atleast 2, the groups represented by each of R17, R₁₈ and R₁₉ may beidentical or different.

In formulae (10) to (15), R₅, R₆, r5 and r6 are as defined for formula(1), with r5=r6=0 being preferred.

Illustrative, non-limiting examples of the compound of formula (1) aregiven below. Formulae (16) through (27) are general formulae. Tables 1through 12 show combinations of R groups an formulae (16) through (27),respectively. In these Tables, except for Ar₁ to Ar₆, where all R groupsunder the same heading are hydrogen atoms, it is shown simply by H.Where there is a substituent, only the substituent is shown, indicatingthat the remaining are hydrogen atoms.

                                      TABLE 1                                     __________________________________________________________________________     ##STR21##                                                                    Compound                                                                      No.    R.sup.1 ˜R.sup.4                                                                R.sup.5 ˜R.sup.9                                                                            R.sup.10 ˜R.sup.13                                                              R.sup.14 ˜R.sup.18           __________________________________________________________________________    I-1    H       H                   H       H                                  I-2    H       R.sup.6 = CH.sub.3  H       R.sup.17 = CH.sub.3                I-3    H       R.sup.7 = CH.sub.3  H       R.sup.16 = CH.sub.3                I-4    H       R.sup.7 = t-C.sub.4 H.sub.9                                                                       H       R.sup.16 = t-C.sub.4 H.sub.9       I-5    H       R.sup.7 = OCH.sub.3 H       R.sup.16 = OCH.sub.3               I-6    H       R.sup.7 = Ph        H       R.sup.16 = Ph                      I-7    H                                                                                      ##STR22##          H                                                                                      ##STR23##                         I-8    H       R.sup.7 = OPh       H       R.sup.16 = OPh                     I-9    H       R.sup.7 = N(C.sub.2 H.sub.5).sub.2                                                                H       R.sup.16 = N(C.sub.2 H.sub.5).s                                               ub.2                               I-10   H       R.sup.7 = N(Ph).sub.2                                                                             H       R.sup.16 = N(Ph).sub.2             I-11   H       R.sup.7 = Cl        H       R.sup.16 = Cl                      I-12   R.sup.2 = CH.sub.3                                                                    H                   R.sup.11 = CH.sub.3                                                                   H                                  I-13   R.sup.2 = OCH.sub.3                                                                   H                   R11 = OCH.sub.3                                                                       H                                  I-14   R.sup.2 = Ph                                                                          H                   R.sup.11 = Ph                                                                         H                                  I-15   R.sup.2 = OPh                                                                         H                   R.sup.11 = OPh                                                                        H                                  I-16   R.sup.2 = N(C.sub.2 H.sub.5).sub.2                                                    H                   R.sup.11 = N(C.sub.2 H.sub.5).sub.2                                                   H                                  I-17   R.sup.2 = Cl                                                                          H                   R.sup.11 = Cl                                                                         H                                  I-18   H       H                   H       H                                  I-19   H       H                   H       H                                  I-20   H       H                   H       H                                  I-21   H       H                   H       H                                  I-22   H       H                   H       H                                  I-23   R.sup.2 = Ph                                                                          R.sup.7 = Ph        R.sup.11 = Ph                                                                         R.sup.16 = Ph                      I-24   R.sup.2 = N(Ph).sub.2                                                                 H                   R.sup.11 = Ph                                                                         H                                  I-25   H       R.sup.6 = CH.sub.3  H       R.sup.16 = CH.sub.3                I-26   H       R.sup.6 = R.sup.8 = CH.sub.3                                                                      H       H                                  I-27   H       R.sup.6 = R.sup.8 = CH.sub.3                                                                      H       H                                  I-28   H       R.sup.7 = N(Ph).sub.2                                                                             H       R.sup.16 = N(Ph).sub.2             I-29   H       R.sup.6 = N(Ph).sub.2                                                                             H       R.sup.17 = N(Ph).sub.2             I-30   H                                                                                      ##STR24##          H                                                                                      ##STR25##                         I-31   H                                                                                      ##STR26##          H                                                                                      ##STR27##                         I-32   H                                                                                      ##STR28##          H                                                                                      ##STR29##                         I-33   H       R.sup.6 = Ph        H       R.sup.17 = Ph                      I-34   H       R.sup.7 = N(Ph).sub.2                                                                             H       H                                  I-35   H       R.sup.6 = N(Ph).sub.2                                                                             H       H                                  I-36   H                                                                                      ##STR30##          H                                                                                      ##STR31##                         I-37   H                                                                                      ##STR32##          H                                                                                      ##STR33##                         I-38   H                                                                                      ##STR34##          H                                                                                      ##STR35##                         I-39   H                                                                                      ##STR36##          H                                                                                      ##STR37##                         I-40   H                                                                                      ##STR38##          H                                                                                      ##STR39##                         I-41   H                                                                                      ##STR40##          H                                                                                      ##STR41##                         I-42   H                                                                                      ##STR42##          H                                                                                      ##STR43##                         I-43   H                                                                                      ##STR44##          H                                                                                      ##STR45##                         I-44   H                                                                                      ##STR46##          H                                                                                      ##STR47##                         I-45   H                                                                                      ##STR48##          H                                                                                      ##STR49##                         I-46   H                                                                                      ##STR50##          H                                                                                      ##STR51##                         I-47   H                                                                                      ##STR52##          H                                                                                      ##STR53##                         __________________________________________________________________________    Compound                                                                      No.    R.sup.19 ˜R.sup.22                                                               R.sup.23 ˜R.sup.27                                                                    R.sup.28 ˜R.sup.31                                                               R.sup.32 ˜R.sup.36                                                                   R.sup.37 ˜R.sup.                                                        44                        __________________________________________________________________________    I-1    H        H             H        H            H                         I-2    H        R.sup.26 = CH.sub.3                                                                         H        R.sup.35 = CH.sub.3                                                                        H                         I-3    H        R.sup.25 = CH.sub.3                                                                         H        R.sup.34 = CH.sub.3                                                                        H                         I-4    H        R.sup.25 = t-C.sub.4 H.sub.9                                                                H        R.sup.34 = t-C.sub.4 H.sub.9                                                               H                         I-5    H        R.sup.25 = OCH.sub.3                                                                        H        R.sup.34 = OCH.sub.3                                                                       H                         I-6    H        R.sup.25 = Ph H        R.sup.34 = Ph                                                                              H                         I-7    H                                                                                       ##STR54##    H                                                                                       ##STR55##   H                         I-8    H        R.sup.25 = OPh                                                                              H        R.sup.34 = OPh                                                                             H                         I-9    H        R.sup.25 = N(C.sub.2 H.sub.5).sub.2                                                         H        R.sup.34 = N(C.sub.2 H.sub.5).sub.2                                           1            H                         I-10   H        R.sup.25 = N(Ph).sub.2                                                                      H        R.sup.34 = N(Ph).sub.2                                                                     H                         I-11   H        R.sup.25 = Cl H        R.sup.34 = Cl                                                                              H                         I-12   R.sup.20 = CH.sub.3                                                                    H             R.sup.29 = CH.sub.3                                                                    H            H                         I-13   R.sup.20 = OCH.sub.3                                                                   H             R.sup.29 = OCH.sub.3                                                                   H            H                         I-14   R.sup.20 = Ph                                                                          H             R.sup.29 = Ph                                                                          H            H                         I-15   R.sup.20 = OPh                                                                         H             R.sup.29 = OPh                                                                         H            H                         I-16   R.sup.20 = N(C.sub.2 H.sub.5).sub.2                                                    H             R.sup.29 = N(C.sub.2 H.sub.5).sub.2                                                    H            H                         I-17   R.sup.20 = Cl                                                                          H             R.sup.29 = Cl                                                                          H            H                         I-18   H        H             H        H            R.sup.37 = R.sup.42 =                                                         CH.sub.3                  I-19   H        H             H        H            R.sup.38 = R.sup.43 =                                                         OCH.sub.3                 I-20   H        H             H        H            R.sup.38 = R.sup.43 =                                                         N(CH.sub.3).sub.2         I-21   H        H             H        H            R.sup.38 = R.sup.43 =                                                         Cl                        I-22   H        H             H        H            R.sup.40 = R.sup.43 =                                                         CH.sub.3                  I-23   R.sup.20 = Ph                                                                          R.sup.25 = Ph R.sup.29 = Ph                                                                          R.sup.34 = Ph                                                                              H                         I-24   R.sup.20 = Ph                                                                          H             R.sup.29 = Ph                                                                          H            H                         I-25   H        R.sup.26 = CH.sub.3                                                                         H        R.sup.34 = CH.sub.3                                                                        H                         I-26   H        R.sup.24 = R.sup.26 = CH.sub.3                                                              H        H            H                         I-27   H        H             H        R.sup.34 = R.sup.36                                                                        H CH.sub.3                I-28   H        H             H        H            H                         I-29   H        H             H        H            H                         I-30   H        H             H        H            H                         I-31   H        H             H        H            H                         I-32   H        H             H        H            H                         I-33   H        R.sup.26 = Ph H        R.sup.35 = Ph                                                                              H                         I-34   H        R.sup.25 = N(Ph).sub.2                                                                      H        H            H                         I-35   H        R.sup.26 = N(Ph).sub.2                                                                      H        H            H                         I-36   H        H             H        H            H                         I-37   H        H             H        H            H                         I-38   H        H             H        H            H                         I-39   H        H             H        H            H                         I-40   H        H             H        H            H                         I-41   H        H             H        H            H                         I-42   H        H             H        H            H                         I-43   H        H             H        H            H                         I-44   H        H             H        H            H                         I-45   H        H             H        H            H                         I-46   H        H             H        H            H                         I-47   H        H             H        H            H                         __________________________________________________________________________

                                      TABLE 1                                     __________________________________________________________________________    Compound                                                                      No.    R.sup.1 ˜R.sup.4                                                                R.sup.5 ˜R.sup.9                                                                            R.sup.10 ˜R.sup.13                                                              R.sup.14 ˜R.sup.18           __________________________________________________________________________    I-1    H       H                   H       H                                  I-2    H       R.sup.6 = CH.sub.3  H       R.sup.17 = CH.sub.3                I-3    H       R.sup.7 = CH.sub.3  H       R.sup.16 = CH.sub.3                I-4    H       R.sup.7 = t-C.sub.4 H.sub.9                                                                       H       R.sup.16 = t-C.sub.4 H.sub.9       I-5    H       R.sup.7 = OCH.sub.3 H       R.sup.16 = OCH.sub.3               I-6    H       R.sup.7 = Ph        H       R.sup.16 = Ph                      I-7    H                                                                                      ##STR56##          H                                                                                      ##STR57##                         I-8    H       R.sup.7 = OPh       H       R.sup.16 = OPh                     I-9    H       R.sup.7 = N(C.sub.2 H.sub.5).sub.2                                                                H       R.sup.16 = N(C.sub.2 H.sub.5).s                                               ub.2                               I-10   H       R.sup.7 = N(Ph).sub.2                                                                             H       R.sup.16 = N(Ph).sub.2             I-11   H       R.sup.7 = Cl        H       R.sup.16 = Cl                      I-12   R.sup.2 = CH.sub.3                                                                    H                   R.sup.11 = CH.sub.3                                                                   H                                  I-13   R.sup.2 = OCH.sub.3                                                                   H                   R11 = OCH.sub.3                                                                       H                                  I-14   R.sup.2 = Ph                                                                          H                   R.sup.11 = Ph                                                                         H                                  I-15   R.sup.2 = OPh                                                                         H                   R.sup.11 = OPh                                                                        H                                  I-16   R.sup.2 = N(C.sub.2 H.sub.5).sub.2                                                    H                   R.sup.11 = N(C.sub.2 H.sub.5).sub.2                                                   H                                  I-17   R.sup.2 = Cl                                                                          H                   R.sup.11 = Cl                                                                         H                                  I-18   H       H                   H       H                                  I-19   H       H                   H       H                                  I-20   H       H                   H       H                                  I-21   H       H                   H       H                                  I-22   H       H                   H       H                                  I-23   R.sup.2 = Ph                                                                          R.sup.7 = Ph        R.sup.11 = Ph                                                                         R.sup.16 = Ph                      I-24   R.sup.2 = N(Ph).sub.2                                                                 H                   R.sup.11 = Ph                                                                         H                                  I-25   H       R.sup.6 = CH.sub.3  H       R.sup.16 = CH.sub.3                I-26   H       R.sup.6 = R.sup.8 = CH.sub.3                                                                      H       H                                  I-27   H       R.sup.6 = R.sup.8 = CH.sub.3                                                                      H       H                                  I-28   H       R.sup.7 = N(Ph).sub.2                                                                             H       R.sup.16 = N(Ph).sub.2             I-29   H       R.sup.6 = N(Ph).sub.2                                                                             H       R.sup.17 = N(Ph).sub.2             I-30   H                                                                                      ##STR58##          H                                                                                      ##STR59##                         I-31   H                                                                                      ##STR60##          H                                                                                      ##STR61##                         I-32   H                                                                                      ##STR62##          H                                                                                      ##STR63##                         I-33   H       R.sup.6 = Ph        H       R.sup.17 = Ph                      I-34   H       R.sup.7 = N(Ph).sub.2                                                                             H       H                                  I-35   H       R.sup.6 = N(Ph).sub.2                                                                             H       H                                  I-36   H                                                                                      ##STR64##          H                                                                                      ##STR65##                         I-37   H                                                                                      ##STR66##          H                                                                                      ##STR67##                         I-38   H                                                                                      ##STR68##          H                                                                                      ##STR69##                         I-39   H                                                                                      ##STR70##          H                                                                                      ##STR71##                         I-40   H                                                                                      ##STR72##          H                                                                                      ##STR73##                         I-41   H                                                                                      ##STR74##          H                                                                                      ##STR75##                         I-42   H                                                                                      ##STR76##          H                                                                                      ##STR77##                         I-43   H                                                                                      ##STR78##          H                                                                                      ##STR79##                         I-44   H                                                                                      ##STR80##          H                                                                                      ##STR81##                         I-45   H                                                                                      ##STR82##          H                                                                                      ##STR83##                         I-46   H                                                                                      ##STR84##          H                                                                                      ##STR85##                         I-47   H                                                                                      ##STR86##          H                                                                                      ##STR87##                         __________________________________________________________________________    Compound                                                                      No.    R.sup.19 ˜R.sup.22                                                               R.sup.23 ˜R.sup.27                                                                    R.sup.28 ˜R.sup.31                                                               R.sup.32 ˜R.sup.36                                                                   R.sup.37 ˜R.sup.                                                        44                        __________________________________________________________________________    I-1    H        H             H        H            H                         I-2    H        R.sup.26 = CH.sub.3                                                                         H        R.sup.35 = CH.sub.3                                                                        H                         I-3    H        R.sup.25 = CH.sub.3                                                                         H        R.sup.34 = CH.sub.3                                                                        H                         I-4    H        R.sup.25 = t-C.sub.4 H.sub.9                                                                H        R.sup.34 = t-C.sub.4 H.sub.9                                                               H                         I-5    H        R.sup.25 = OCH.sub.3                                                                        H        R.sup.34 = OCH.sub.3                                                                       H                         I-6    H        R.sup.25 = Ph H        R.sup.34 = Ph                                                                              H                         I-7    H                                                                                       ##STR88##    H                                                                                       ##STR89##   H                         I-8    H        R.sup.25 = OPh                                                                              H        R.sup.34 = OPh                                                                             H                         I-9    H        R.sup.25 = N(C.sub.2 H.sub.5).sub.2                                                         H        R.sup.34 = N(C.sub.2 H.sub.5).sub.2                                                        H                         I-10   H        R.sup.25 = N(Ph).sub.2                                                                      H        R.sup.34 = N(Ph).sub.2                                                                     H                         I-11   H        R.sup.25 = Cl H        R.sup.34 = Cl                                                                              H                         I-12   R.sup.20 = CH.sub.3                                                                    H             R.sup.29 = CH.sub.3                                                                    H            H                         I-13   R.sup.20 = OCH.sub.3                                                                   H             R.sup.29 = OCH.sub.3                                                                   H            H                         I-14   R.sup.20 = Ph                                                                          H             R.sup.29 = Ph                                                                          H            H                         I-15   R.sup.20 = OPh                                                                         H             R.sup.29 = OPh                                                                         H            H                         I-16   R.sup.20 = N(C.sub.2 H.sub.5).sub.2                                                    H             R.sup.29 = N(C.sub.2 H.sub.5).sub.2                                                    H            H                         I-17   R.sup.20 = Cl                                                                          H             R.sup.29 = Cl                                                                          H            H                         I-18   H        H             H        H            R.sup.37 = R.sup.42 =                                                         CH.sub.3                  I-19   H        H             H        H            R.sup.38 = R.sup.43 =                                                         OCH.sub.3                 I-20   H        H             H        H            R.sup.38 = R.sup.43 =                                                         N(CH.sub.3).sub.2         I-21   H        H             H        H            R.sup.38 = R.sup.43 =                                                         Cl                        I-22   H        H             H        H            R.sup.40 = R.sup.43 =                                                         CH.sub.3                  I-23   R.sup.20 = Ph                                                                          R.sup.25 = Ph R.sup.29 = Ph                                                                          R.sup.34 = Ph                                                                              H                         I-24   R.sup.20 = Ph                                                                          H             R.sup.29 = Ph                                                                          H            H                         I-25   H        R.sup.26 = CH.sub.3                                                                         H        R.sup.34 = CH.sub.3                                                                        H                         I-26   H        R.sup.24 = R.sup.26 = CH.sub.3                                                              H        H            H                         I-27   H        H             H        R.sup.34 = R.sup.36                                                                        H CH.sub.3                I-28   H        H             H        H            H                         I-29   H        H             H        H            H                         I-30   H        H             H        H            H                         I-31   H        H             H        H            H                         I-32   H        H             H        H            H                         I-33   H        R.sup.26 = Ph H        R.sup.35 = Ph                                                                              H                         I-34   H        R.sup.25 = N(Ph).sub.2                                                                      H        H            H                         I-35   H        R.sup.26 = N(Ph).sub.2                                                                      H        H            H                         I-36   H        H             H        H            H                         I-37   H        H             H        H            H                         I-38   H        H             H        H            H                         I-39   H        H             H        H            H                         I-40   H        H             H        H            H                         I-41   H        H             H        H            H                         I-42   H        H             H        H            H                         I-43   H        H             H        H            H                         I-44   H        H             H        H            H                         I-45   H        H             H        H            H                         I-46   H        H             H        H            H                         I-47   H        H             H        H            H                         __________________________________________________________________________     ##STR90##                                                                 

                                      TABLE 2                                     __________________________________________________________________________    Compound                                                                      No.    R.sup.51 ˜R.sup.54                                                              R.sup.55 ˜R.sup.59                                                                          R.sup.60 ˜R.sup.63                                                              R.sup.64 ˜R.sup.68           __________________________________________________________________________    II-1   H       H                   H       H                                  II-2   H       R.sup.56 = CH.sub.3 H       R.sup.65 = CH.sub.3                II-3   H       R.sup.57 = CH.sub.3 H       R.sup.66 = CH.sub.3                II-4   H       R.sup.57 = t-C.sub.4 H.sub.9                                                                      H       R.sup.66 = t-C.sub.4 H.sub.9       II-5   H       R.sup.57 = OCH.sub.3                                                                              H       R.sup.66 = OCH.sub.3               II-6   H       R.sup.57 = Ph       H       R.sup.66 = Ph                      II-7   H                                                                                      ##STR91##          H                                                                                      ##STR92##                         II-8   H       R.sup.57 = OPh      H       R.sup.66 = OPh                     II-9   H       R.sup.57 = N(C.sub.2 H.sub.5).sub.2                                                               H       R.sup.66 = N(C.sub.2 H.sub.5).s                                               ub.2                               II-10  H       R.sup.57 = N(Ph).sub.2                                                                            H       R.sup.66 = N(Ph).sub.2             II-11  H       R.sup.57 = Cl       H       R.sup.66 = Cl                      II-12  H                                                                                      ##STR93##          H                                                                                      ##STR94##                         II-13  R.sup.52 = CH.sub.3                                                                   H                   R.sup.62 = CH.sub.3                                                                   H                                  II-14  R.sup.52 = OCH.sub.3                                                                  H                   R.sup.62 = OCH.sub.3                                                                  H                                  II-15  R.sup.52 = Ph                                                                         H                   R.sup.62 = Ph                                                                         H                                  II-16  R.sup.52 = OPh                                                                        H                   R.sup.62 = OPh                                                                        H                                  II-17  R.sup.52 = N(C.sub.2 H.sub.5).sub.2                                                   H                   R.sup.62 = N(C.sub.2 H.sub.5).sub.2                                                   H                                  II-18  R.sup.52 = Cl                                                                         H                   R.sup.62 = Cl                                                                         H                                  II-19  H       H                   H       H                                  II-20  H       H                   H       H                                  II-21  H       H                   H       H                                  II-22  H       H                   H       H                                  II-23  H       H                   H       H                                  II-24  H       R.sup.57 = CH.sub.3 H       R.sup.65 = CH.sub.3                II-25  H       R.sup.56 = R.sup.58 = CH.sub.3                                                                    H       H                                  II-26  H       R.sup.57 = CH.sub.3 H       R.sup.66 = CH.sub.3                II-27  H       R.sup.56 = R.sup.58 = CH.sub.3                                                                    H       R.sup.65 = R.sup.67                                                           = CH.sub.3                         II-28  H       R.sup.57 = N(Ph).sub.2                                                                            H       R.sup.66 = N(Ph).sub.2             II-29  H                                                                                      ##STR95##          H                                                                                      ##STR96##                         II-30  H                                                                                      ##STR97##          H                                                                                      ##STR98##                         II-31  H       R.sup.58 = N(Ph).sub.2                                                                            H       R.sup.65 = N(Ph).sub.2             II-32  H                                                                                      ##STR99##          H                                                                                      ##STR100##                        II-33  H                                                                                      ##STR101##         H                                                                                      ##STR102##                        II-34  H                                                                                      ##STR103##         H                                                                                      ##STR104##                        II-35  H                                                                                      ##STR105##         H                                                                                      ##STR106##                        II-36  H                                                                                      ##STR107##         H                                                                                      ##STR108##                        II-37  H                                                                                      ##STR109##         H                                                                                      ##STR110##                        II-38  H                                                                                      ##STR111##         H                                                                                      ##STR112##                        II-39  H                                                                                      ##STR113##         H                                                                                      ##STR114##                        II-40  H                                                                                      ##STR115##         H                                                                                      ##STR116##                        II-41  H                                                                                      ##STR117##         H                                                                                      ##STR118##                        II-42  H       R.sup.57 = N(Ph).sub.2                                                                            H       H                                  II-43  H                                                                                      ##STR119##         H                                                                                      ##STR120##                        II-44  H                                                                                      ##STR121##         H                                                                                      ##STR122##                        __________________________________________________________________________    Compound                                                                      No.    R.sup.69 ˜R.sup.72                                                               R.sup.73 ˜R.sup.77                                                                    R.sup.78 ˜R.sup.81                                                               R.sup.82 ˜R.sup.86                                                                   R.sup.37 ˜R.sup.                                                        44                        __________________________________________________________________________    II-1   H        H             H        H            H                         II-2   H        R.sup.74 = CH.sub.3                                                                         H        R.sup.83 = CH.sub.3                                                                        H                         II-3   H        R.sup.75 = CH.sub.3                                                                         H        R.sup.84 = CH.sub.3                                                                        H                         II-4   H        R.sup.75 = t-C.sub.4 H.sub.9                                                                H        R.sup.84 = t-C.sub.4 H.sub.9                                                               H                         II-5   H        R.sup.75 = OCH.sub.3                                                                        H        R.sup.84 = OCH.sub.3                                                                       H                         II-6   H        R.sup.75 = Ph H        R.sup.84 = Ph                                                                              H                         II-7   H                                                                                       ##STR123##   H                                                                                       ##STR124##  H                         II-8   H        R.sup.75 = OPh                                                                              H        R.sup.84 = OPh                                                                             H                         II-9   H        R.sup.75 = N(C.sub.2 H.sub.5).sub.2                                                         H        R.sup.84 = N(C.sub.2 H.sub.5).sub.2                                                        H                         II-10  H        R.sup.75 = N(Ph).sub.2                                                                      H        R.sup.84 = N(Ph).sub.2                                                                     H                         II-11  H        R.sup.75 = Cl H        R.sup.84 = Cl                                                                              H                         II-12  H                                                                                       ##STR125##   H                                                                                       ##STR126##  H                         II-13  R.sup.72 = CH.sub.3                                                                    H             R.sup.79 = CH.sub.3                                                                    H            H                         II-14  R.sup.72 = OCH.sub.3                                                                   H             R.sup.79 = OCH.sub.3                                                                   H            H                         II-15  R.sup.72 = Ph                                                                          H             R.sup.79 = Ph                                                                          H            H                         II-16  R.sup.72 = OPh                                                                         H             R.sup.79 = OPh                                                                         H            H                         II-17  R.sup.72 = N(C.sub.2 H.sub.5).sub.2                                                    H             R.sup.79 = N(C.sub.2 H.sub.5).sub.2                                                    H            H                         II-18  R.sup.72 = Cl                                                                          H             R.sup.79 = Cl                                                                          H            H                         II-19  H        H             H        H            R.sup.37 = R.sup.42 =                                                         CH.sub.3                  II-20  H        H             H        H            R.sup.38 = R.sup.43 =                                                         OCH.sub.3                 II-21  H        H             H        H            R.sup.38 = R.sup.43 =                                                         N(CH.sub.3).sub.2         II-22  H        H             H        H            R.sup.38 = R.sup.43 =                                                         Cl                        II-23  H        H             H        H            R.sup.40 = R.sup.43 =                                                         CH.sub.3                  II-24  H        R.sup.75 = CH.sub.3                                                                         H        R.sup.83 = CH.sub.3                                                                        H                         II-25  H        R.sup.74 = R.sup.76 = CH.sub.3                                                              H        H            H                         II-26  H        R.sup.74 = CH.sub.3                                                                         H        R.sup.85 = CH.sub.3                                                                        H                         II-27  H        H             H        H            H                         II-28  H        H             H        H            H                         II-29  H        H             H        H            H                         II-30  H        H             H        H            H                         II-31  H        H             H        H            H                         II-32  H        H             H        H            H                         II-33  H        H             H        H            H                         II-34  H        H             H        H            H                         II-35  H        H             H        H            H                         II-36  H        H             H        H            H                         II-37  H        H             H        H            H                         II-38  H        H             H        H            H                         II-39  H        H             H        H            H                         II-40  H        H             H        H            H                         II-41  H        H             H        H            H                         II-42  H        R.sup.75 = N(Ph).sub.2 H                                                                    H        H            H                         II-43  H        H             H        H            H                         II-44  H        H             H        H            H                         __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________     ##STR127##                                                                   Compound                                                                      No.   R.sup.51 ˜R.sup.54                                                               R.sup.55 ˜R.sup.59                                                                   R.sup.10 ˜R.sup.13                                                                    R.sup.14 ˜R.sup.18                                                                   R.sup.69 ˜R.s                                                           up.72                  __________________________________________________________________________    III-1 H        H            H             H            H                      III-2 H        R.sup.58 = CH.sub.3                                                                        H             R.sup.17 = CH.sub.3                                                                        H                      III-3 H        R.sup.57 = CH.sub.3                                                                        H             R.sup.16 = CH.sub.3                                                                        H                      III-4 H        R.sup.58 = t-C.sub.4 H.sub.9                                                               H             R.sup.17 = t-C.sub.4 H.sub.9                                                               H                      III-5 H        R.sup.58 = OCH.sub.3                                                                       H             R.sup.17 = OCH.sub.3                                                                       H                      III-6 H        R.sup.59 = Ph                                                                              H             R.sup.16 = Ph                                                                              H                      III-7 H                                                                                       ##STR128##  H                                                                                            ##STR129##  H                      III-8 H        R.sup.58 = OPh                                                                             H             R.sup.17 = OPh                                                                             H                      III-9 H        R.sup.58 = N(C.sub.2 H.sub.5).sub.2                                                        H             R.sup.17 = N(C.sub.2 H.sub.5).su                                              b.2          H                      III-10                                                                              H        R.sup.58 = N(Ph).sub.2                                                                     H             R.sup.17 = N(Ph).sub.2                                                                     H                      III-11                                                                              H        R.sup.58 = Cl                                                                              H             R.sup.17 = Cl                                                                              H                      III-12                                                                              R.sup.52 = CH.sub.3                                                                    H            R.sup.11 = CH.sub.3                                                                         H            R.sup.72 =                                                                    CH.sub.3               III-13                                                                              R.sup.52 = OCH.sub.3                                                                   H            R.sup.11 = OCH.sub.3                                                                        H            R.sup.72 =                                                                    OCH.sub.3              III-14                                                                              R.sup.52 = Ph                                                                          H            R.sup.11 = Ph H            R.sup.72 = Ph          III-15                                                                              R.sup.52 = OPh                                                                         H            R.sup.11 = OPh                                                                              H            R.sup.72 = OPh         III-16                                                                              R.sup.52 = N(C.sub.2 H.sub.5).sub.2                                                    H            R.sup.11 = N(C.sub.2 H.sub.5).sub.2                                                         H            R.sup.72 =                                                                    N(C.sub.2 H.sub.5).                                                           sub.2                  III-17                                                                              R.sup.52 = Cl                                                                          H            R.sup.11 = Cl H            R.sup.72 = Cl          III-18                                                                              H        H            H             H            H                      III-19                                                                              H        H            H             H            H                      III-20                                                                              H        H            H             H            H                      III-21                                                                              H        H            H             H            H                      III-22                                                                              H        H            H             H            H                      III-23                                                                              H        R.sup.57 = CH.sub.3                                                                        H             R.sup.16 = CH.sub.3                                                                        H                      III-24                                                                              H        R.sup.57 = CH.sub.3                                                                        H             R.sup.17 = CH.sub.3                                                                        H                      III-25                                                                              H        H            H             H            H                      III-26                                                                              H        H            H             H            H                      III-27                                                                              H        H            H             H            H                      III-28                                                                              H        H            H             H            H                      III-29                                                                              H        H            H             H            H                      III-30                                                                              H        H            H             H            H                      III-31                                                                              H        H            H             H            H                      III-32                                                                              H        H            H             H            H                      III-33                                                                              H        H            H             H            H                      III-34                                                                              H        H            H             H            H                      III-35                                                                              H        H            H             H            H                      III-36                                                                              H        H            H             H            H                      III-37                                                                              H        H            H             H            H                      III-38                                                                              H        H            H             H            H                      III-39                                                                              H        H            R.sup.11 = Ph H            H                      III-40                                                                              H        H                                                                                           ##STR130##   H            H                      III-41                                                                              H        H                                                                                           ##STR131##   H            H                      __________________________________________________________________________    Compound                                                                      No.   R.sup.73 ˜R.sup.77                                                                          R.sup.78 ˜R.sup.81                                                              R.sup.82 ˜R.sup.86                                                                         R.sup.37 ˜R.sup                                                         .44                      __________________________________________________________________________    III-1 H                   H       H                  H                        III-2 R.sup.76 = CH.sub.3 H       R.sup.83 = CH.sub.3                                                                              H                        III-3 R.sup.75 = CH.sub.3 H       R.sup.84 = CH.sub.3                                                                              H                        III-4 R.sup.76 = t-C.sub.4 H.sub.9                                                                      H       R.sup.83 = t-C.sub.4 H.sub.9                                                                     H                        III-5 R.sup.76 = OCH.sub.3                                                                              H       R.sup.83 = OCH.sub.3                                                                             H                        III-6 R.sup.75 = Ph       H       R.sup.84 = Ph      H                        III-7                                                                                ##STR132##         H                                                                                      ##STR133##        H                        III-8 R.sup.76 = OPh      H       R.sup.83 = OPh     H                        III-9 R.sup.76 = N(C.sub.2 H.sub.5).sub.2                                                               H       R.sup.83 = N(C.sub.2 H.sub.5).sub.2                                                              H                        III-10                                                                              R.sup.76 = N(Ph).sub.2                                                                            H       R.sup.83 = N(Ph).sub.2                                                                           H                        III-11                                                                              R.sup.76 = Cl       H       R.sup.83 = Cl      H                        III-12                                                                              H                   R.sup.79 = CH.sub.3                                                                   H                  H                        III-13                                                                              H                   R.sup.79 = OCH.sub.3                                                                  H                  H                        III-14                                                                              H                   R.sup.79 = Ph                                                                         H                  H                        III-15                                                                              H                   R.sup.79 = OPh                                                                        H                  H                        III-16                                                                              H                   R.sup.79 = N(C.sub.2 H.sub.5).sub.2                                                   H                  H                        III-17                                                                              H                   R.sup.79 = Cl                                                                         H                  H                        III-18                                                                              H                   H       H                  R.sup.37 = R.sup.42                                                           = CH.sub.3               III-19                                                                              H                   H       H                  R.sup.38 = R.sup.41                                                           = CH.sub.3               III-20                                                                              H                   H       H                  R.sup.38 = R.sup.41                                                           = OCH.sub.3              III-21                                                                              H                   H       H                  R.sup.38 = R.sup.41                                                           = N(CH.sub.3).sub.2      III-22                                                                              H                   H       H                  R.sup.38 = R.sup.41                                                           = Cl                     III-23                                                                              R.sup.74 = CH.sub.3 H       R.sup.85 = CH.sub.3                                                                              H                        III-24                                                                              R.sup.75 = CH.sub.3 H       R.sup.85 = CH.sub.3                                                                              H                        III-25                                                                              R.sup.75 = N(Ph).sub.2                                                                            H       R.sup.84 = N(Ph).sub.2                                                                           H                        III-26                                                                              R.sup.76 = N(Ph).sub.2                                                                            H       R.sup.83 = N(Ph).sub.2                                                                           H                        III-27                                                                               ##STR134##         H                                                                                      ##STR135##        H                        III-28                                                                               ##STR136##         H                                                                                      ##STR137##        H                        III-29                                                                               ##STR138##         H                                                                                      ##STR139##        H                        III-30                                                                               ##STR140##         H                                                                                      ##STR141##        H                        III-31                                                                               ##STR142##         H                                                                                      ##STR143##        H                        III-32                                                                               ##STR144##         H                                                                                      ##STR145##        H                        III-33                                                                               ##STR146##         H                                                                                      ##STR147##        H                        III-34                                                                               ##STR148##         H                                                                                      ##STR149##        H                        III-35                                                                               ##STR150##         H                                                                                      ##STR151##        H                        III-36                                                                               ##STR152##         H                                                                                      ##STR153##        H                        III-37                                                                               ##STR154##         H                                                                                      ##STR155##        H                        III-38                                                                               ##STR156##         H                                                                                      ##STR157##        H                        III-39                                                                              H                   H       H                  H                        III-40                                                                              H                   H       H                  H                        III-41                                                                              H                   H       H                  H                        __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________    Compound                                                                      No.   R.sup.51 ˜R.sup.54                                                               R.sup.55 ˜R.sup.59                                                                   R.sup.10 ˜R.sup.13                                                                    R.sup.14 ˜R.sup.18                                                                   R.sup.69 ˜R.s                                                           up.72                  __________________________________________________________________________    III-1 H        H            H             H            H                      III-2 H        R.sup.58 = CH.sub.3                                                                        H             R.sup.17 = CH.sub.3                                                                        H                      III-3 H        R.sup.57 = CH.sub.3                                                                        H             R.sup.16 = CH.sub.3                                                                        H                      III-4 H        R.sup.58 = t-C.sub.4 H.sub.9                                                               H             R.sup.17 = t-C.sub.4 H.sub.9                                                               H                      III-5 H        R.sup.58 = OCH.sub.3                                                                       H             R.sup.17 = OCH.sub.3                                                                       H                      III-6 H        R.sup.59 = Ph                                                                              H             R.sup.16 = Ph                                                                              H                      III-7 H                                                                                       ##STR158##  H                                                                                            ##STR159##  H                      III-8 H        R.sup.58 = OPh                                                                             H             R.sup.17 = OPh                                                                             H                      III-9 H        R.sup.58 = N(C.sub.2 H.sub.5).sub.2                                                        H             R.sup.17 = N(C.sub.2 H.sub.5).su                                              b.2          H                      III-10                                                                              H        R.sup.58 = N(Ph).sub.2                                                                     H             R.sup.17 = N(Ph).sub.2                                                                     H                      III-11                                                                              H        R.sup.58 = Cl                                                                              H             R.sup.17 = Cl                                                                              H                      III-12                                                                              R.sup.52 = CH.sub.3                                                                    H            R.sup.11 = CH.sub.3                                                                         H            R.sup.72 =                                                                    CH.sub.3               III-13                                                                              R.sup.52 = OCH.sub.3                                                                   H            R.sup.11 = OCH.sub.3                                                                        H            R.sup.72 =                                                                    OCH.sub.3              III-14                                                                              R.sup.52 = Ph                                                                          H            R.sup.11 = Ph H            R.sup.72 = Ph          III-15                                                                              R.sup.52 = OPh                                                                         H            R.sup.11 = OPh                                                                              H            R.sup.72 = OPh         III-16                                                                              R.sup.52 = N(C.sub.2 H.sub.5).sub.2                                                    H            R.sup.11 = N(C.sub.2 H.sub.5).sub.2                                                         H            R.sup.72 =                                                                    N(C.sub.2 H.sub.5).                                                           sub.2                  III-17                                                                              R.sup.52 = Cl                                                                          H            R.sup.11 = Cl H            R.sup.72 = Cl          III-18                                                                              H        H            H             H            H                      III-19                                                                              H        H            H             H            H                      III-20                                                                              H        H            H             H            H                      III-21                                                                              H        H            H             H            H                      III-22                                                                              H        H            H             H            H                      III-23                                                                              H        R.sup.57 = CH.sub.3                                                                        H             R.sup.16 = CH.sub.3                                                                        H                      III-24                                                                              H        R.sup.57 = CH.sub.3                                                                        H             R.sup.17 = CH.sub.3                                                                        H                      III-25                                                                              H        H            H             H            H                      III-26                                                                              H        H            H             H            H                      III-27                                                                              H        H            H             H            H                      III-28                                                                              H        H            H             H            H                      III-29                                                                              H        H            H             H            H                      III-30                                                                              H        H            H             H            H                      III-31                                                                              H        H            H             H            H                      III-32                                                                              H        H            H             H            H                      III-33                                                                              H        H            H             H            H                      III-34                                                                              H        H            H             H            H                      III-35                                                                              H        H            H             H            H                      III-36                                                                              H        H            H             H            H                      III-37                                                                              H        H            H             H            H                      III-38                                                                              H        H            H             H            H                      III-39                                                                              H        H            R.sup.11 = Ph H            H                      III-40                                                                              H        H                                                                                           ##STR160##   H            H                      III-41                                                                              H        H                                                                                           ##STR161##   H            H                      __________________________________________________________________________    Compound                                                                      No.   R.sup.73 ˜R.sup.77                                                                          R.sup.78 ˜R.sup.81                                                              R.sup.82 ˜R.sup.86                                                                         R.sup.37 ˜R.sup                                                         .44                      __________________________________________________________________________    III-1 H                   H       H                  H                        III-2 R.sup.76 = CH.sub.3 H       R.sup.83 = CH.sub.3                                                                              H                        III-3 R.sup.75 = CH.sub.3 H       R.sup.84 = CH.sub.3                                                                              H                        III-4 R.sup.76 = t-C.sub.4 H.sub.9                                                                      H       R.sup.83 = t-C.sub.4 H.sub.9                                                                     H                        III-5 R.sup.76 = OCH.sub.3                                                                              H       R.sup.83 = OCH.sub.3                                                                             H                        III-6 R.sup.75 = Ph       H       R.sup.84 = Ph      H                        III-7                                                                                ##STR162##         H                                                                                      ##STR163##        H                        III-8 R.sup.76 = OPh      H       R.sup.83 = OPh     H                        III-9 R.sup.76 = N(C.sub.2 H.sub.5).sub.2                                                               H       R.sup.83 = N(C.sub.2 H.sub.5).sub.2                                                              H                        III-10                                                                              R.sup.76 = N(Ph).sub.2                                                                            H       R.sup.83 = N(Ph).sub.2                                                                           H                        III-11                                                                              R.sup.76 = Cl       H       R.sup.83 = Cl      H                        III-12                                                                              H                   R.sup.79 = CH.sub.3                                                                   H                  H                        III-13                                                                              H                   R.sup.79 = OCH.sub.3                                                                  H                  H                        III-14                                                                              H                   R.sup.79 = Ph                                                                         H                  H                        III-15                                                                              H                   R.sup.79 = OPh                                                                        H                  H                        III-16                                                                              H                   R.sup.79 = N(C.sub.2 H.sub.5).sub.2                                                   H                  H                        III-17                                                                              H                   R.sup.79 = Cl                                                                         H                  H                        III-18                                                                              H                   H       H                  R.sup.37 = R.sup.42                                                           = CH.sub.3               III-19                                                                              H                   H       H                  R.sup.38 = R.sup.41                                                           = CH.sub.3               III-20                                                                              H                   H       H                  R.sup.38 = R.sup.41                                                           = OCH.sub.3              III-21                                                                              H                   H       H                  R.sup.38 = R.sup.41                                                           = N(CH.sub.3).sub.2      III-22                                                                              H                   H       H                  R.sup.38 = R.sup.41                                                           = Cl                     III-23                                                                              R.sup.74 = CH.sub.3 H       R.sup.85 = CH.sub.3                                                                              H                        III-24                                                                              R.sup.75 = CH.sub.3 H       R.sup.85 = CH.sub.3                                                                              H                        III-25                                                                              R.sup.75 = N(Ph).sub.2                                                                            H       R.sup.84 = N(Ph).sub.2                                                                           H                        III-26                                                                              R.sup.76 = N(Ph).sub.2                                                                            H       R.sup.83 = N(Ph).sub.2                                                                           H                        III-27                                                                               ##STR164##         H                                                                                      ##STR165##        H                        III-28                                                                               ##STR166##         H                                                                                      ##STR167##        H                        III-29                                                                               ##STR168##         H                                                                                      ##STR169##        H                        III-30                                                                               ##STR170##         H                                                                                      ##STR171##        H                        III-31                                                                               ##STR172##         H                                                                                      ##STR173##        H                        III-32                                                                               ##STR174##         H                                                                                      ##STR175##        H                        III-33                                                                               ##STR176##         H                                                                                      ##STR177##        H                        III-34                                                                               ##STR178##         H                                                                                      ##STR179##        H                        III-35                                                                               ##STR180##         H                                                                                      ##STR181##        H                        III-36                                                                               ##STR182##         H                                                                                      ##STR183##        H                        III-37                                                                               ##STR184##         H                                                                                      ##STR185##        H                        III-38                                                                               ##STR186##         H                                                                                      ##STR187##        H                        III-39                                                                              H                   H       H                  H                        III-40                                                                              H                   H       H                  H                        III-41                                                                              H                   H       H                  H                        __________________________________________________________________________

    TABLE 4                                                                          -                                                                              ##STR188##                                                                     Compound                                                                       No. R.sup.1 ˜R.sup.4 R.sup.5 ˜R.sup.9 R.sup.10                     ˜R.sup.13 R.sup.14 ˜R.sup.18 R.sup.69 ˜R.sup.72             R.sup.73 ˜R.sup.77 R.sup.78 ˜R.sup.81 R.sup.82                      ˜R.sup.86 R.sup.37                                                       ˜R.sup.44                                                                IV-1 H H H H H H H H H                                                         IV-2 H R.sup.6 = CH.sub.3 H R.sup.17 = CH.sub.3 H R.sup.76 = CH.sub.3 H       R.sup.83 =                                                                      CH.sub.3 H                                                     IV-3 H         R.sup.7 = CH.sub.3 H R.sup.16 = CH.sub.3 H R.sup.75 = CH.sub.3 H               R.sup.84 =                                                                      CH.sub.3 H                                                     IV-4 H         R.sup.6 = t-C.sub.4 H.sub.9 H R.sup.17 = t-C.sub.4 H.sub.9 H R.sup.76 =        t-C.sub.4 H.sub.9 H R.sup.83 = t-C.sub.4                                        H.sub.9 H                        IV-5 H R.sup.6 = OCH.sub.3 H R.sup.17        = OCH.sub.3 H R.sup.76 = OCH.sub.3 H R.sup.83 =                                 OCH.sub.3 H                                                                                                                  IV-6 H                           ##STR189##                                                                     H                                                                              ##STR190##                                                                     H                                                                              ##STR191##                                                                     H                                                                              ##STR192##                                                                     H                                                                             IV-7 H R.sup.6 = OPh H R.sup.17 = OPh H R.sup.76 = OPh H R.sup.83 = OPh        H                                                                               IV-8 H R.sup.6 = N(C.sub.2 H.sub.5).sub.2 H R.sup.17 = N(C.sub.2              H.sub.5).sub.2 H R.sup.76 = N(C.sub.2 H.sub.5).sub.2 H R.sup.83 =              N(C.sub.2                                                                       H.sub.5).sub.2 H                                                IV-9 H        R.sup.6 = N(Ph).sub.2 H R.sup.17 = N(Ph).sub.2 H R.sup.76 = N(Ph).sub.2        H R.sup.83 =                                                                    N(Ph).sub.2 H                                                IV-10 H          R.sup.6 = Cl H R.sup.17 = Cl H R.sup.76 = Cl H R.sup.83 =                       Cl H            IV-11 H R.sup.7 = Ph H R.sup.16 = Ph H R.sup.75 = Ph H        R.sup.84 =                                                                      Ph H                                                           IV-12          R.sup.2 = CH.sub.3 H R.sup.11 =                                                 CH.sub.3 H H H H H H                      IV-13 R.sup.2 = OCH.sub.3 H         R.sup.11 =                                                                      OCH.sub.3 H H H H H H                                          IV-14          R.sup.2 = Ph H R.sup.11 =                                                       Ph H H H H H H                                  IV-15 R.sup.2 = OPh H         R.sup.11 =                                                                      OPh H H H H H H                                                IV-16          R.sup.2 = N(C.sub.2 H.sub.5).sub.2 H R.sup.11 = N(C.sub.2 H.sub.5).sub.2       H H H H H H                                                                     IV-17 R.sup.2 = Cl H R.sup.11 =                                                Cl H H H H H H                           IV-18 H H H H H H H H R.sup.38       = R.sup.41 =                                                                    CH.sub.3                                                     IV-19 H H        H H H H H H R.sup.38 = R.sup.41 =                                               OCH.sub.3                               IV-20 H H H H H H H H R.sup.38        = R.sup.41 =                                                                    N(CH.sub.3).sub.2                                            IV-21 H H        H H H H H H R.sup.38 = R.sup.41 =                                               Cl                                      IV-22 H R.sup.5 = CH.sup.3 H          R.sup.17 = CH.sup.3 H R.sup.75 = CH.sup.3 H R.sup.84 = CH.sup.3 H                      IV-23 H R.sup.6 = CH.sup.3 H R.sup.16 = CH.sup.3 H R.sup.76 =          CH.sup.3 H R.sup.84 =                                                           CH.sup.3 H                                          IV-24 H H H H H           R.sup.75 = N(Ph).sub.2 H R.sup.84 =                                             N(Ph).sub.2 H                         IV-25 H H H H H R.sup.76 =              N(Ph).sub.2 H R.sup.83 =                                                        N(Ph).sub.2 H                                                                                         IV-26 H H H H H                                         ##STR193##                                                                     H                                                                              ##STR194##                                                                     H                                                                             IV-27 H H H H H                                                                 ##STR195##                                                                     H                                                                              ##STR196##                                                                     H                                                                             IV-28 H H H H H                                                                 ##STR197##                                                                     H                                                                              ##STR198##                                                                     H                                                                             IV-29 H H H H H                                                                 ##STR199##                                                                     H                                                                              ##STR200##                                                                     H                                                                             IV-30 H H H H H                                                                 ##STR201##                                                                     H                                                                              ##STR202##                                                                     H                                                                             IV-31 H H H H H                                                                 ##STR203##                                                                     H                                                                              ##STR204##                                                                     H                                                                             IV-32 H H H H H                                                                 ##STR205##                                                                     H                                                                              ##STR206##                                                                     H                                                                             IV-33 H H H H H                                                                 ##STR207##                                                                     H                                                                              ##STR208##                                                                     H                                                                             IV-34 H H H H H                                                                 ##STR209##                                                                     H                                                                              ##STR210##                                                                     H                                                                             IV-35 H H H H H                                                                 ##STR211##                                                                     H                                                                              ##STR212##                                                                     H                                                                             IV-36 H H H H H                                                                 ##STR213##                                                                     H                                                                              ##STR214##                                                                     H                                                                             IV-37 H H H H H                                                                 ##STR215##                                                                     H                                                                              ##STR216##                                                                     H                                                                             IV-38 H H H H H                                                                 ##STR217##                                                                     H                                                                              ##STR218##                                                                     H                                                                             IV-39 H H H H H                                                                 ##STR219##                                                                     H                                                                              ##STR220##                                                                     H                                                                             IV-40 H H H H H                                                                 ##STR221##                                                                     H                                                                              ##STR222##                                                                     H                                                                             IV-41 H H H H H R.sup.76 = N(CH.sub.3).sub.2 H R.sup.84 =                       N(CH.sub.3).sub.2 H                                                           IV-42 H H H H H                                                                 ##STR223##                                                                     H                                                                              ##STR224##                                                                     H                                                                             IV-43 H H H H H R.sup.75 = CH.sub.3 H R.sup.84 =                                CH.sub.3 H               IV-44 H H H H H R.sup.74 = CH.sub.3 H R.sup.83       =                                                                               CH.sub.3 H                                                                    IV-45 H R.sup.6 = CH.sub.3 H R.sup.15 =                                         CH.sub.3 H H H H H                IV-46 H R.sup.7 = CH.sub.3 H R.sup.17       =                                                                               CH.sub.3 H H H H H                                                            IV-47 H R.sup.6 = Ph H R.sup.15 =                                               Ph H H H H H                            IV-48 H H H H H R.sup.75 =            OCH.sub.3 H R.sup.84 =                                                          OCH.sub.3 H                                        IV-49 H H H H H            R.sup.75 = Ph H R.sup.84 =                                                      Ph H                                           IV-50 H H H H H H H H          R.sup.37 = R.sup.42 =                                                           CH.sub.3                                                                                           IV-51 H H H H H                                            ##STR225##                                                                     H                                                                              ##STR226##                                                                     H                                                                        

    TABLE 4                                                                          - Compound                                                                     No. R.sup.1 ˜R.sup.4 R.sup.5 ˜R.sup.9 R.sup.10                     ˜R.sup.13 R.sup.14 ˜R.sup.18 R.sup.69 ˜R.sup.72             R.sup.73 ˜R.sup.77 R.sup.78 ˜R.sup.81 R.sup.82                      ˜R.sup.86 R.sup.37                                                       ˜R.sup.44                                                                IV-1 H H H H H H H H H                                                         IV-2 H R.sup.6 = CH.sub.3 H R.sup.17 = CH.sub.3 H R.sup.76 = CH.sub.3 H       R.sup.83 =                                                                      CH.sub.3 H                                                     IV-3 H         R.sup.7 = CH.sub.3 H R.sup.16 = CH.sub.3 H R.sup.75 = CH.sub.3 H               R.sup.84 =                                                                      CH.sub.3 H                                                     IV-4 H         R.sup.6 = t-C.sub.4 H.sub.9 H R.sup.17 = t-C.sub.4 H.sub.9 H R.sup.76 =        t-C.sub.4 H.sub.9 H R.sup.83 = t-C.sub.4                                        H.sub.9 H                        IV-5 H R.sup.6 = OCH.sub.3 H R.sup.17        = OCH.sub.3 H R.sup.76 = OCH.sub.3 H R.sup.83 =                                 OCH.sub.3 H                                                                                                                  IV-6 H                           ##STR227##                                                                     H                                                                              ##STR228##                                                                     H                                                                              ##STR229##                                                                     H                                                                              ##STR230##                                                                     H                                                                             IV-7 H R.sup.6 = OPh H R.sup.17 = OPh H R.sup.76 = OPh H R.sup.83 = OPh        H                                                                               IV-8 H R.sup.6 = N(C.sub.2 H.sub.5).sub.2 H R.sup.17 = N(C.sub.2              H.sub.5).sub.2 H R.sup.76 = N(C.sub.2 H.sub.5).sub.2 H R.sup.83 =              N(C.sub.2                                                                       H.sub.5).sub.2 H                                                IV-9 H        R.sup.6 = N(Ph).sub.2 H R.sup.17 = N(Ph).sub.2 H R.sup.76 = N(Ph).sub.2        H R.sup.83 =                                                                    N(Ph).sub.2 H                                                IV-10 H          R.sup.6 = Cl H R.sup.17 = Cl H R.sup.76 = Cl H R.sup.83 =                       Cl H            IV-11 H R.sup.7 = Ph H R.sup.16 = Ph H R.sup.75 = Ph H        R.sup.84 =                                                                      Ph H                                                           IV-12          R.sup.2 = CH.sub.3 H R.sup.11 =                                                 CH.sub.3 H H H H H H                      IV-13 R.sup.2 = OCH.sub.3 H         R.sup.11 =                                                                      OCH.sub.3 H H H H H H                                          IV-14          R.sup.2 = Ph H R.sup.11 =                                                       Ph H H H H H H                                  IV-15 R.sup.2 = OPh H         R.sup.11 =                                                                      OPh H H H H H H                                                IV-16          R.sup.2 = N(C.sub.2 H.sub.5).sub.2 H R.sup.11 = N(C.sub.2 H.sub.5).sub.2       H H H H H H                                                                     IV-17 R.sup.2 = Cl H R.sup.11 =                                                Cl H H H H H H                           IV-18 H H H H H H H H R.sup.38       = R.sup.41 =                                                                    CH.sub.3                                                     IV-19 H H        H H H H H H R.sup.38 = R.sup.41 =                                               OCH.sub.3                               IV-20 H H H H H H H H R.sup.38        = R.sup.41 =                                                                    N(CH.sub.3).sub.2                                            IV-21 H H        H H H H H H R.sup.38 = R.sup.41 =                                               Cl                                      IV-22 H R.sup.5 = CH.sup.3 H          R.sup.17 = CH.sup.3 H R.sup.75 = CH.sup.3 H R.sup.84 = CH.sup.3 H                      IV-23 H R.sup.6 = CH.sup.3 H R.sup.16 = CH.sup.3 H R.sup.76 =          CH.sup.3 H R.sup.84 =                                                           CH.sup.3 H                                          IV-24 H H H H H           R.sup.75 = N(Ph).sub.2 H R.sup.84 =                                             N(Ph).sub.2 H                         IV-25 H H H H H R.sup.76 =              N(Ph).sub.2 H R.sup.83 =                                                        N(Ph).sub.2 H                                                                                         IV-26 H H H H H                                         ##STR231##                                                                     H                                                                              ##STR232##                                                                     H                                                                             IV-27 H H H H H                                                                 ##STR233##                                                                     H                                                                              ##STR234##                                                                     H                                                                             IV-28 H H H H H                                                                 ##STR235##                                                                     H                                                                              ##STR236##                                                                     H                                                                             IV-29 H H H H H                                                                 ##STR237##                                                                     H                                                                              ##STR238##                                                                     H                                                                             IV-30 H H H H H                                                                 ##STR239##                                                                     H                                                                              ##STR240##                                                                     H                                                                             IV-31 H H H H H                                                                 ##STR241##                                                                     H                                                                              ##STR242##                                                                     H                                                                             IV-32 H H H H H                                                                 ##STR243##                                                                     H                                                                              ##STR244##                                                                     H                                                                             IV-33 H H H H H                                                                 ##STR245##                                                                     H                                                                              ##STR246##                                                                     H                                                                             IV-34 H H H H H                                                                 ##STR247##                                                                     H                                                                              ##STR248##                                                                     H                                                                             IV-35 H H H H H                                                                 ##STR249##                                                                     H                                                                              ##STR250##                                                                     H                                                                             IV-36 H H H H H                                                                 ##STR251##                                                                     H                                                                              ##STR252##                                                                     H                                                                             IV-37 H H H H H                                                                 ##STR253##                                                                     H                                                                              ##STR254##                                                                     H                                                                             IV-38 H H H H H                                                                 ##STR255##                                                                     H                                                                              ##STR256##                                                                     H                                                                             IV-39 H H H H H                                                                 ##STR257##                                                                     H                                                                              ##STR258##                                                                     H                                                                             IV-40 H H H H H                                                                 ##STR259##                                                                     H                                                                              ##STR260##                                                                     H                                                                             IV-41 H H H H H R.sup.76 = N(CH.sub.3).sub.2 H R.sup.84 =                       N(CH.sub.3).sub.2 H                                                           IV-42 H H H H H                                                                 ##STR261##                                                                     H                                                                              ##STR262##                                                                     H                                                                             IV-43 H H H H H R.sup.75 = CH.sub.3 H R.sup.84 =                                CH.sub.3 H               IV-44 H H H H H R.sup.74 = CH.sub.3 H R.sup.83       =                                                                               CH.sub.3 H                                                                    IV-45 H R.sup.6 = CH.sub.3 H R.sup.15 =                                         CH.sub.3 H H H H H                IV-46 H R.sup.7 = CH.sub.3 H R.sup.17       =                                                                               CH.sub.3 H H H H H                                                            IV-47 H R.sup.6 = Ph H R.sup.15 =                                               Ph H H H H H                            IV-48 H H H H H R.sup.75 =            OCH.sub.3 H R.sup.84 =                                                          OCH.sub.3 H                                        IV-49 H H H H H            R.sup.75 = Ph H R.sup.84 =                                                      Ph H                                           IV-50 H H H H H H H H          R.sup.37 = R.sup.42 =                                                           CH.sub.3                                                                                           IV-51 H H H H H                                            ##STR263##                                                                     H                                                                              ##STR264##                                                                     H                                                                        

    TABLE 5                                                                          -                                                                              ##STR265##                                                                     Compound                                                                       No. R.sup.51 ˜R.sup.54 R.sup.55 ˜R.sup.59 R.sup.10                 ˜R.sup.13 R.sup.14 ˜R.sup.18 R.sup.69 ˜R.sup.72             R.sup.73 ˜R.sup.77 R.sup.28 ˜R.sup.31 R.sup.32                      ˜R.sup.36 R.sup.37                                                       ˜R.sup.44                                                                V-1 H H H H H H H H H                                                          V-2 H R.sup.58 = CH.sub.3 H R.sup.17 = CH.sub.3 H R.sup.76 = CH.sub.3 H       R.sup.35 =                                                                      CH.sub.3 H                                                     V-3 H          R.sup.57 = CH.sub.3 H R.sup.16 = CH.sub.3 H R.sup.75 = CH.sub.3 H              R.sup.34 =                                                                      CH.sub.3 H                                                     V-4 H          R.sup.58 = t-C.sub.4 H.sub.9 H R.sup.17 = t-C.sub.4 H.sub.9 H R.sup.76 =       t-C.sub.4 H.sub.9 H R.sup.35 = t-C.sub.4                                        H.sub.9 H                        V-5 H R.sup.58 = OCH.sub.3 H R.sup.17        = OCH.sub.3 H R.sup.76 = OCH.sub.3 H R.sup.35 =                                 OCH.sub.3 H                                                                                                                  V-6 H                            ##STR266##                                                                     H                                                                              ##STR267##                                                                     H                                                                              ##STR268##                                                                     H                                                                              ##STR269##                                                                     H                                                                             V-7 H R.sup.58 = OPh H R.sup.17 = OPh H R.sup.76 = OPh H R.sup.35 = OPh        H                                                                               V-8 H R.sup.58 = N(C.sub.2 H.sub.5).sub.2 H R.sup.17 = N(C.sub.2              H.sub.5).sub.2 H R.sup.76 = N(C.sub.2 H.sub.5).sub.2 H R.sup.35 =              N(C.sub.2                                                                       H.sub.5).sub.2 H                                                V-9 H         R.sup.58 = N(Ph).sub.2 H R.sup.17 = N(Ph).sub.2 H R.sup.76 = N(Ph).sub.2       H R.sup.35 =                                                                    N(Ph).sub.2 H                                                V-10 H           R.sup.58 = Cl H R.sup.17 = Cl H R.sup.76 = Cl H R.sup.35 =                      Cl H           V-11 H R.sup.57 = Ph H R.sup.16 = Ph H R.sup.75 = Ph H         R.sup.34 =                                                                      Ph H                                                           V-12 H         R.sup.57 = CH.sub.3 H R.sup.16 = CH.sub.3 H R.sup.76 = CH.sub.3 H              R.sup.35 =                                                                      CH.sub.3 H                                                     V-13 H         R.sup.57 = CH.sub.3 H R.sup.17 = CH.sub.3 H R.sup.75 = CH.sub.3 H              R.sup.36 =                                                                      CH.sub.3 H                                                     V-14 H H       R.sup.11 = CH.sub.3 H H H H R.sup.29 =                                          CH.sub.3 H                         V-15 H H R.sup.11 = OCH.sub.3 H H H        H R.sup.29 =                                                                    OCH.sub.3 H                                                  V-16 H H         R.sup.11 = Ph H H H R.sup.29 =                                                  Ph H H                                     V-17 H H R.sup.11 = OPh H H        H R.sup.29 =                                                                    OPh H H                                                      V-18 H H         R.sup.11 = N(C.sub.2 H.sub.5).sub.2 H H H R.sup.29 = N(C.sub.2                  H.sub.5).sub.2 H H                                                             V-19 H H R.sup.11 = Cl H H H R.sup.29 =                                        Cl H H                           V-20 H H H H H H H H R.sup.38 =              R.sup.41 =                                                                      CH.sub.3                                                       V-21 H H       H H H H H H R.sup.38 = R.sup.41 =                                               OCH.sub.3                               V-22 H H H H H H H H R.sup.38 =       R.sup.41 =                                                                      N(CH.sub.3).sub.2                                              V-23 H H       H H H H H H R.sup.38 = R.sup.41 =                                               Cl                                      V-24 H R.sup.57 = N(Ph).sub.2 H       H H R.sup.75 =                                                                  N(Ph).sub.2 H H H                                          V-25 H             R.sup.58 = N(Ph).sub.2 H H H R.sup.76 =                                         N(Ph).sub.2 H H H                                                                                                    V-26 H                                   ##STR270##                                                                     H H H                                                                          ##STR271##                                                                     H H H                                                                         V-27 H                                                                          ##STR272##                                                                     H H H                                                                          ##STR273##                                                                     H H H                                                                         V-28 H                                                                          ##STR274##                                                                     H H H                                                                          ##STR275##                                                                     H H H                                                                         V-29 H                                                                          ##STR276##                                                                     H H H                                                                          ##STR277##                                                                     H H H                                                                         V-30 H                                                                          ##STR278##                                                                     H H H                                                                          ##STR279##                                                                     H H H                                                                         V-31 H                                                                          ##STR280##                                                                     H H H                                                                          ##STR281##                                                                     H H H                                                                          V-32 H                                                                         ##STR282##                                                                     H H H                                                                          ##STR283##                                                                     H H H                                                                         V-33 H                                                                          ##STR284##                                                                     H H H                                                                          ##STR285##                                                                     H H H                                                                         V-34 H                                                                          ##STR286##                                                                     H H H                                                                          ##STR287##                                                                     H H H                                                                          V-35 H                                                                         ##STR288##                                                                     H H H                                                                          ##STR289##                                                                     H H H                                                                         V-36 H                                                                          ##STR290##                                                                     H H H                                                                          ##STR291##                                                                     H H H                                                                          V-37 H                                                                         ##STR292##                                                                     H H H                                                                          ##STR293##                                                                     H H H                                                                         V-38 H R.sup.57 = CH.sub.3 H H H R.sup.75 =                                     CH.sub.3 H H H                V-39 H R.sup.56 = CH.sub.3 H H H R.sup.74       =                                                                               CH.sub.3 H H H                                                                V-40 H R.sup.57 = OCH.sub.3 H H H R.sup.75 =                                    OCH.sub.3 H H H                                                                                             V-41 H                                            ##STR294##                                                                     H H H                                                                          ##STR295##                                                                     H H H                                                                          V-42 H                                                                         ##STR296##                                                                     H H H                                                                          ##STR297##                                                                     H H H                                                                          V-43 H                                                                         ##STR298##                                                                     H H H                                                                          ##STR299##                                                                     H H H                                                                         V-44 H R.sup.57 = N(CH.sub.3).sub.2 H H H R.sup.57 = N(CH.sub.3).sub.2 H       H H                                                                             V-45 H H H R.sup.17 = Ph H H H R.sup.33 =                                      Ph H                                                                     

    TABLE 5                                                                          - Compound                                                                     No. R.sup.51 ˜R.sup.54 R.sup.55 ˜R.sup.59 R.sup.10                 ˜R.sup.13 R.sup.14 ˜R.sup.18 R.sup.69 ˜R.sup.72             R.sup.73 ˜R.sup.77 R.sup.28 ˜R.sup.31 R.sup.32                      ˜R.sup.36 R.sup.37                                                       ˜R.sup.44                                                                V-1 H H H H H H H H H                                                          V-2 H R.sup.58 = CH.sub.3 H R.sup.17 = CH.sub.3 H R.sup.76 = CH.sub.3 H       R.sup.35 =                                                                      CH.sub.3 H                                                     V-3 H          R.sup.57 = CH.sub.3 H R.sup.16 = CH.sub.3 H R.sup.75 = CH.sub.3 H              R.sup.34 =                                                                      CH.sub.3 H                                                     V-4 H          R.sup.58 = t-C.sub.4 H.sub.9 H R.sup.17 = t-C.sub.4 H.sub.9 H R.sup.76 =       t-C.sub.4 H.sub.9 H R.sup.35 = t-C.sub.4                                        H.sub.9 H                        V-5 H R.sup.58 = OCH.sub.3 H R.sup.17        = OCH.sub.3 H R.sup.76 = OCH.sub.3 H R.sup.35 =                                 OCH.sub.3 H                                                                                                                  V-6 H                            ##STR300##                                                                     H                                                                              ##STR301##                                                                     H                                                                              ##STR302##                                                                     H                                                                              ##STR303##                                                                     H                                                                             V-7 H R.sup.58 = OPh H R.sup.17 = OPh H R.sup.76 = OPh H R.sup.35 = OPh        H                                                                               V-8 H R.sup.58 = N(C.sub.2 H.sub.5).sub.2 H R.sup.17 = N(C.sub.2              H.sub.5).sub.2 H R.sup.76 = N(C.sub.2 H.sub.5).sub.2 H R.sup.35 =              N(C.sub.2                                                                       H.sub.5).sub.2 H                                                V-9 H         R.sup.58 = N(Ph).sub.2 H R.sup.17 = N(Ph).sub.2 H R.sup.76 = N(Ph).sub.2       H R.sup.35 =                                                                    N(Ph).sub.2 H                                                V-10 H           R.sup.58 = Cl H R.sup.17 = Cl H R.sup.76 = Cl H R.sup.35 =                      Cl H           V-11 H R.sup.57 = Ph H R.sup.16 = Ph H R.sup.75 = Ph H         R.sup.34 =                                                                      Ph H                                                           V-12 H         R.sup.57 = CH.sub.3 H R.sup.16 = CH.sub.3 H R.sup.76 = CH.sub.3 H              R.sup.35 =                                                                      CH.sub.3 H                                                     V-13 H         R.sup.57 = CH.sub.3 H R.sup.17 = CH.sub.3 H R.sup.75 = CH.sub.3 H              R.sup.36 =                                                                      CH.sub.3 H                                                     V-14 H H       R.sup.11 = CH.sub.3 H H H H R.sup.29 =                                          CH.sub.3 H                         V-15 H H R.sup.11 = OCH.sub.3 H H H        H R.sup.29 =                                                                    OCH.sub.3 H                                                  V-16 H H         R.sup.11 = Ph H H H R.sup.29 =                                                  Ph H H                                     V-17 H H R.sup.11 = OPh H H        H R.sup.29 =                                                                    OPh H H                                                      V-18 H H         R.sup.11 = N(C.sub.2 H.sub.5).sub.2 H H H R.sup.29 = N(C.sub.2                  H.sub.5).sub.2 H H                                                             V-19 H H R.sup.11 = Cl H H H R.sup.29 =                                        Cl H H                           V-20 H H H H H H H H R.sup.38 =              R.sup.41 =                                                                      CH.sub.3                                                       V-21 H H       H H H H H H R.sup.38 = R.sup.41 =                                               OCH.sub.3                               V-22 H H H H H H H H R.sup.38 =       R.sup.41 =                                                                      N(CH.sub.3).sub.2                                              V-23 H H       H H H H H H R.sup.38 = R.sup.41 =                                               Cl                                      V-24 H R.sup.57 = N(Ph).sub.2 H       H H R.sup.75 =                                                                  N(Ph).sub.2 H H H                                          V-25 H             R.sup.58 = N(Ph).sub.2 H H H R.sup.76 =                                         N(Ph).sub.2 H H H                                                                                                    V-26 H                                   ##STR304##                                                                     H H H                                                                          ##STR305##                                                                     H H H                                                                         V-27 H                                                                          ##STR306##                                                                     H H H                                                                          ##STR307##                                                                     H H H                                                                         V-28 H                                                                          ##STR308##                                                                     H H H                                                                          ##STR309##                                                                     H H H                                                                         V-29 H                                                                          ##STR310##                                                                     H H H                                                                          ##STR311##                                                                     H H H                                                                         V-30 H                                                                          ##STR312##                                                                     H H H                                                                          ##STR313##                                                                     H H H                                                                         V-31 H                                                                          ##STR314##                                                                     H H H                                                                          ##STR315##                                                                     H H H                                                                         V-32 H                                                                          ##STR316##                                                                     H H H                                                                          ##STR317##                                                                     H H H                                                                         V-33 H                                                                          ##STR318##                                                                     H H H                                                                          ##STR319##                                                                     H H H                                                                         V-34 H                                                                          ##STR320##                                                                     H H H                                                                          ##STR321##                                                                     H H H                                                                         V-35 H                                                                          ##STR322##                                                                     H H H                                                                          ##STR323##                                                                     H H H                                                                         V-36 H                                                                          ##STR324##                                                                     H H H                                                                          ##STR325##                                                                     H H H                                                                         V-37 H                                                                          ##STR326##                                                                     H H H                                                                          ##STR327##                                                                     H H H                                                                         V-38 H R.sup.57 = CH.sub.3 H H H R.sup.75 =                                     CH.sub.3 H H H                V-39 H R.sup.56 = CH.sub.3 H H H R.sup.74       =                                                                               CH.sub.3 H H H                                                                V-40 H R.sup.57 = OCH.sub.3 H H H R.sup.75 =                                    OCH.sub.3 H H H                                                                                                           V-41 H                              ##STR328##                                                                     H H H                                                                          ##STR329##                                                                     H H H                                                                         V-42 H                                                                          ##STR330##                                                                     H H H                                                                          ##STR331##                                                                     H H H                                                                         V-43 H                                                                          ##STR332##                                                                     H H H                                                                          ##STR333##                                                                     H H H                                                                         V-44 H R.sup.57 = N(CH.sub.3).sub.2 H H H R.sup.57 = N(CH.sub.3).sub.2 H       H H                                                                             V-45 H H H R.sup.17 = Ph H H H R.sup.33 =                                      Ph H                                                                     

    TABLE 6                                                                          -                                                                              ##STR334##                                                                     Compound                                                                       No. R.sup.1 ˜R.sup.4 R.sup.5 ˜R.sup.9 R.sup.10                     ˜R.sup.13 R.sup.14 ˜R.sup.18 R.sup.19 ˜R.sup.22             R.sup.22 ˜R.sup.27 R.sup.78 ˜R.sup.81 R.sup.82                      ˜R.sup.86 R.sup.37                                                       ˜R.sup.44                                                                VI-1 H H H H H H H H H                                                         VI-2 H R.sup.8  = CH.sub.3 H R.sup.17  = CH.sub.3 H R.sup.26  =               CH.sub.3 H R.sup.83  =                                                          CH.sub.3 H                                         VI-3 H R.sup.7  =          CH.sub.3 H R.sup.16  = CH.sub.3 H R.sup.25  = CH.sub.3 H R.sup.84  =           CH.sub.3 H                                                                      VI-4 H R.sup.6  = t-C.sub.4 H.sub.9 H R.sup.17  = t-C.sub.4 H.sub.9 H         R.sup.26  = t-C.sub.4 H.sub.9 H R.sup.88  = t-C.sub.4                           H.sub.9 H           VI-5 H R.sup.8  = OCH.sub.3 H R.sup.17  = OCH.sub.3       H R.sup.26  = OCH.sub.3 H R.sup.83                                              =OCH.sub.3 H                                                                                                     VI-6 H                                       ##STR335##                                                                     H                                                                              ##STR336##                                                                     H                                                                              ##STR337##                                                                     H                                                                              ##STR338##                                                                     H                                                                             VI-7 H R.sup.6  = OPh H R.sup.17  = OPh H R.sup.26  = OPh H R.sup.83  =        OPh H                                                                           VI-8 H R.sup.6  = N(C.sub.2 H.sub.5).sub.2 H R.sup.17  = N(C.sub.2            H.sub.5).sub.2 H R.sup.26  = N(C.sub.2 H.sub.5).sub.2 H R.sup.83  =            N(C.sub.2                                                                       H.sub.5).sub.2 H                                                VI-9 H        R.sup.6  = N(Ph).sub.2 H R.sup.17  = N(Ph).sub.2 H R.sup.26  =                  N(Ph).sub.2 H R.sup.83  =                                                      N(Ph).sub.2 H                                  VI-10 H R.sup.6  = Cl H        R.sup.17  = Cl H R.sup.26  = Cl H R.sup.83  =                                   Cl H                        VI-11 H R.sup.7  = Ph H R.sup.16  = Ph H          R.sup.25  = Ph H R.sup.84  =                                                    Ph H                                         VI-12 R.sup.2  = CH.sub.3        H R.sup.11  = CH.sub.3 H R.sup.20  =                                            CH.sub.3 H H H H                     VI-13 R.sup.2  = OCH.sub.3 H             R.sup.11  = OCH.sub.3 H R.sup.20  =                                             OCH.sub.3 H H H H                     VI-14 R.sup.2  = Ph H R.sup.11  =       Ph H R.sup.20  =                                                                Ph H H H H                                               VI-15 R.sup.2        = OPh H R.sup.11  = OPh H R.sup.20  =                                           OPh H H H H                         VI-16 R.sup.2  = N(C.sub.2                 H.sub.5).sub.2 H R.sup.11  = N(C.sub.2 H.sub.5).sub.2 H R.sup.20  =           N(C.sub.2                                                                       H.sub.5).sub.2 H H H H                                          VI-17         R.sup.2  = Cl H R.sup.11  = Cl H R.sup.20  =                                    Cl H H H H                   VI-18 H H H H H H H H R.sup.38  = R.sup.41        =                                                                              CH.sub.3                                                                      VI-19 H H H H H H H H R.sup.38  = R.sup.41  =                                   OCH.sub.3                   VI-20 H H H H H H H H R.sup.38  = R.sup.41        =                                                                               N(CH.sub.3).sub.2                                                             VI-21 H H H H H H H H R.sup.38  = R.sup.41  =                                   Cl                          VI-22 H R.sup.6  = CH.sub.3 H R.sup.17  =         CH.sub.3 H R.sup.25  = CH.sub.3 H R.sup.84  =                                   CH.sub.3 H                  VI-23 H R.sup.6  = CH.sub.3 H R.sup.16  =         CH.sub.3 H R.sup.26  = CH.sub.3 H R.sup.84  =                                   CH.sub.3 H                  VI-24 H H H H H R.sup.25  = N(Ph).sub.2 H         R.sup.84  =                                                                     N(Ph).sub.2 H                                                 VI-25 H H       H H H R.sup.26  = N(Ph).sub.2 H R.sup.83  =                                     N(Ph).sub.2 H                                                                                                VI-26 H H H H H                                  ##STR339##                                                                     H                                                                              ##STR340##                                                                     H                                                                              VI-27 H H H H H                                                                ##STR341##                                                                     H                                                                              ##STR342##                                                                     H                                                                             VI-28 H H H H H                                                                 ##STR343##                                                                     H                                                                              ##STR344##                                                                     H                                                                             VI-29 H H H H H                                                                 ##STR345##                                                                     H                                                                              ##STR346##                                                                     H                                                                             VI-30 H H H H H                                                                 ##STR347##                                                                     H                                                                              ##STR348##                                                                     H                                                                             VI-31 H H H H H                                                                 ##STR349##                                                                     H                                                                              ##STR350##                                                                     H                                                                             VI-32 H H H H H                                                                 ##STR351##                                                                     H                                                                              ##STR352##                                                                     H                                                                             VI-33 H H H H H                                                                 ##STR353##                                                                     H                                                                              ##STR354##                                                                     H                                                                             VI-34 H H H H H                                                                 ##STR355##                                                                     H                                                                              ##STR356##                                                                     H                                                                             VI-35 H H H H H                                                                 ##STR357##                                                                     H                                                                              ##STR358##                                                                     H                                                                             VI-36 H H H H H                                                                 ##STR359##                                                                     H                                                                              ##STR360##                                                                     H                                                                             VI-37 H H H H H                                                                 ##STR361##                                                                     H                                                                              ##STR362##                                                                     H                                                                              VI-38 H H H H H H H R.sup.84  =                                                CH.sub.3 H                               VI-39 H H H H H H H R.sup.83         =                                                                               CH.sub.3 H                                                                    VI-40 H H H H H H H R.sup.84  =                                                 Ph H                                      VI-41 H H H H H H H R.sup.84        =                                                                               N(Ph).sub.2 H                                                                 VI-42 H H H H H H H R.sup.84  =                                                 OPh H                                     VI-43 H H H H H H H R.sup.84        =                                                                               OCH.sub.3 H                                                                    VI-44 H H H H H H H                                                            ##STR363##                                                                     H                                                                             VI-45 H H H H H H H                                                             ##STR364##                                                                     H                                                                             VI-46 H H H H H H H                                                             ##STR365##                                                                     H                                                                             VI-47 H H H H H H H R.sup.84  =                                                 N(CH.sub.3).sub.2 H                       VI-48 H R.sup.6  = Ph H             R.sup.15  = Ph H R.sup.24  =                                                    Ph H H H                                     VI-49 H R.sup.6  =               N(Ph).sub.2 H R.sup.16  = N(Ph).sub.2 H R.sup.24  = N(Ph).sub.2 H H H              VI-50 H R.sup.6  = CH.sub.3 H R.sup.15  = CH.sub.3 H R.sup.24  =           CH.sub.3 H H H                                                                  VI-51 H R.sup.7  = CH.sub.3 H R.sup.16  = CH.sub.3 H R.sup.25  =              CH.sub.3 H H H                                                                  VI-52 H R.sup.7  = N(Ph).sub.2 H R.sup.16  = N(Ph).sub.2 H R.sup.25  =        N(Ph).sub.2 H H H                                                         

    TABLE 6                                                                          - Compound                                                                     No. R.sup.1 ˜R.sup.4 R.sup.5 ˜R.sup.9 R.sup.10                     ˜R.sup.13 R.sup.14 ˜R.sup.18 R.sup.19 ˜R.sup.22             R.sup.22 ˜R.sup.27 R.sup.78 ˜R.sup.81 R.sup.82                      ˜R.sup.86 R.sup.37                                                       ˜R.sup.44                                                                VI-1 H H H H H H H H H                                                         VI-2 H R.sup.8  = CH.sub.3 H R.sup.17  = CH.sub.3 H R.sup.26  =               CH.sub.3 H R.sup.83  =                                                          CH.sub.3 H                                         VI-3 H R.sup.7  =          CH.sub.3 H R.sup.16  = CH.sub.3 H R.sup.25  = CH.sub.3 H R.sup.84  =           CH.sub.3 H                                                                      VI-4 H R.sup.6  = t-C.sub.4 H.sub.9 H R.sup.17  = t-C.sub.4 H.sub.9 H         R.sup.26  = t-C.sub.4 H.sub.9 H R.sup.88  = t-C.sub.4                           H.sub.9 H           VI-5 H R.sup.8  = OCH.sub.3 H R.sup.17  = OCH.sub.3       H R.sup.26  = OCH.sub.3 H R.sup.83                                              =OCH.sub.3 H                                                                                                     VI-6 H                                       ##STR366##                                                                     H                                                                              ##STR367##                                                                     H                                                                              ##STR368##                                                                     H                                                                              ##STR369##                                                                     H                                                                             VI-7 H R.sup.6  = OPh H R.sup.17  = OPh H R.sup.26  = OPh H R.sup.83  =        OPh H                                                                           VI-8 H R.sup.6  = N(C.sub.2 H.sub.5).sub.2 H R.sup.17  = N(C.sub.2            H.sub.5).sub.2 H R.sup.26  = N(C.sub.2 H.sub.5).sub.2 H R.sup.83  =            N(C.sub.2                                                                       H.sub.5).sub.2 H                                                VI-9 H        R.sup.6  = N(Ph).sub.2 H R.sup.17  = N(Ph).sub.2 H R.sup.26  =                  N(Ph).sub.2 H R.sup.83  =                                                      N(Ph).sub.2 H                                  VI-10 H R.sup.6  = Cl H        R.sup.17  = Cl H R.sup.26  = Cl H R.sup.83  =                                   Cl H                        VI-11 H R.sup.7  = Ph H R.sup.16  = Ph H          R.sup.25  = Ph H R.sup.84  =                                                    Ph H                                         VI-12 R.sup.2  = CH.sub.3        H R.sup.11  = CH.sub.3 H R.sup.20  =                                            CH.sub.3 H H H H                     VI-13 R.sup.2  = OCH.sub.3 H             R.sup.11  = OCH.sub.3 H R.sup.20  =                                             OCH.sub.3 H H H H                     VI-14 R.sup.2  = Ph H R.sup.11  =       Ph H R.sup.20  =                                                                Ph H H H H                                               VI-15 R.sup.2        = OPh H R.sup.11  = OPh H R.sup.20  =                                           OPh H H H H                         VI-16 R.sup.2  = N(C.sub.2                 H.sub.5).sub.2 H R.sup.11  = N(C.sub.2 H.sub.5).sub.2 H R.sup.20  =           N(C.sub.2                                                                       H.sub.5).sub.2 H H H H                                          VI-17         R.sup.2  = Cl H R.sup.11  = Cl H R.sup.20  =                                    Cl H H H H                   VI-18 H H H H H H H H R.sup.38  = R.sup.41        =                                                                              CH.sub.3                                                                      VI-19 H H H H H H H H R.sup.38  = R.sup.41  =                                   OCH.sub.3                   VI-20 H H H H H H H H R.sup.38  = R.sup.41        =                                                                               N(CH.sub.3).sub.2                                                             VI-21 H H H H H H H H R.sup.38  = R.sup.41  =                                   Cl                          VI-22 H R.sup.6  = CH.sub.3 H R.sup.17  =         CH.sub.3 H R.sup.25  = CH.sub.3 H R.sup.84  =                                   CH.sub.3 H                  VI-23 H R.sup.6  = CH.sub.3 H R.sup.16  =         CH.sub.3 H R.sup.26  = CH.sub.3 H R.sup.84  =                                   CH.sub.3 H                  VI-24 H H H H H R.sup.25  = N(Ph).sub.2 H         R.sup.84  =                                                                     N(Ph).sub.2 H                                                 VI-25 H H       H H H R.sup.26  = N(Ph).sub.2 H R.sup.83  =                                     N(Ph).sub.2 H                                                                                                            VI-26 H H H H H                      ##STR370##                                                                     H                                                                              ##STR371##                                                                     H                                                                             VI-27 H H H H H                                                                 ##STR372##                                                                     H                                                                              ##STR373##                                                                     H                                                                             VI-28 H H H H H                                                                 ##STR374##                                                                     H                                                                              ##STR375##                                                                     H                                                                             VI-29 H H H H H                                                                 ##STR376##                                                                     H                                                                              ##STR377##                                                                     H                                                                             VI-30 H H H H H                                                                 ##STR378##                                                                     H                                                                              ##STR379##                                                                     H                                                                             VI-31 H H H H H                                                                 ##STR380##                                                                     H                                                                              ##STR381##                                                                     H                                                                             VI-32 H H H H H                                                                 ##STR382##                                                                     H                                                                              ##STR383##                                                                     H                                                                             VI-33 H H H H H                                                                 ##STR384##                                                                     H                                                                              ##STR385##                                                                     H                                                                             VI-34 H H H H H                                                                 ##STR386##                                                                     H                                                                              ##STR387##                                                                     H                                                                             VI-35 H H H H H                                                                 ##STR388##                                                                     H                                                                              ##STR389##                                                                     H                                                                             VI-36 H H H H H                                                                 ##STR390##                                                                     H                                                                              ##STR391##                                                                     H                                                                             VI-37 H H H H H                                                                 ##STR392##                                                                     H                                                                              ##STR393##                                                                     H                                                                             VI-38 H H H H H H H R.sup.84  =                                                 CH.sub.3 H                                VI-39 H H H H H H H R.sup.83        =                                                                               CH.sub.3 H                                                                    VI-40 H H H H H H H R.sup.84  =                                                 Ph H                                      VI-41 H H H H H H H R.sup.84        =                                                                               N(Ph).sub.2 H                                                                 VI-42 H H H H H H H R.sup.84  =                                                 OPh H                                     VI-43 H H H H H H H R.sup.84        =                                                                               OCH.sub.3 H                                                                    VI-44 H H H H H H H                                                            ##STR394##                                                                     H                                                                             VI-45 H H H H H H H                                                             ##STR395##                                                                     H                                                                             VI-46 H H H H H H H                                                             ##STR396##                                                                     H                                                                             VI-47 H H H H H H H R.sup.84  =                                                 N(CH.sub.3).sub.2 H                       VI-48 H R.sup.6  = Ph H             R.sup.15  = Ph H R.sup.24  =                                                    Ph H H H                                     VI-49 H R.sup.6  =               N(Ph).sub.2 H R.sup.16  = N(Ph).sub.2 H R.sup.24  = N(Ph).sub.2 H H H              VI-50 H R.sup.6  = CH.sub.3 H R.sup.15  = CH.sub.3 H R.sup.24  =           CH.sub.3 H H H                                                                  VI-51 H R.sup.7  = CH.sub.3 H R.sup.16  = CH.sub.3 H R.sup.25  =              CH.sub.3 H H H                                                                  VI-52 H R.sup.7  = N(Ph).sub.2 H R.sup.16  = N(Ph).sub.2 H R.sup.25  =        N(Ph).sub.2 H H H                                                         

    TABLE 7                                                                          -                                                                              ##STR397##                                                                     Compound                                                                       No. Ar.sub.1 Ar.sub.2 R.sup.101 ˜R.sup.104 R.sup.105                     ˜R.sup.108 R.sup.109 ˜R.sup.113 R.sup.114 ˜R.sup.118        R.sup.37                                                                        ˜R.sup.44                                                                      VII-1 Ph Ph H H H H H                                                    VII-2 Ph Ph H H R.sup.110  = CH.sub.3 R.sup.115  =                             CH.sub.3 H            VII-3 Ph Ph H H R.sup.111  = CH.sub.3 R.sup.116         =                                                                               CH.sub.3 H                                                                    VII-4 Ph Ph H H R.sup.110  = t-C.sub.4 H.sub.9 R.sup.115  = t-C.sub.4          H.sub.9 H                                                                       VII-5 Ph Ph H H R.sup.110  = OCH.sub.3 R.sup.115  = OCH.sub.3 H                        VII-6 Ph Ph H H R.sup.111  = Ph R.sup.115  =                           H H                 VII-7 Ph Ph H H                                            ##STR398##                                                                     ##STR399##                                                                     H                                                                             VII-8 Ph Ph H H R.sup.110  = OPh R.sup.115  =                                   OPh H                       VII-9 Ph Ph H H R.sup.110  = N(C.sub.2            H.sub.5).sub.2 R.sup.115  = N(C.sub.2                                           H.sub.5).sub.2 H                    VII-10 Ph Ph H H R.sup.110  =             N(Ph).sub.2 R.sup.115  =                                                        N(Ph).sub.2 H                                    VII-11 Ph Ph H H             R.sup.110  = Cl R.sup.115  =                                                    Cl H                                         VII-12 Ph Ph R.sup.102  =        CH.sub.3 R.sup.106  =                                                           CH.sub.3 H H H                                      VII-13 Ph Ph H H          R.sup.111  = CH.sub.3 R.sup.115  =                                              CH.sub.3 H                             VII-14 Ph Ph H H R.sup.111  =          OCH.sub.3 R.sup.115  =                                                          OCH.sub.3 H                                        VII-15 Ph Ph               R.sup.102  = OCH.sub.3 R.sup.106  =                                             OCH.sub.3 H H H                       VII-16 Ph Ph R.sup.102  = Ph            R.sup.106  =                                                                    Ph H H H                                                     VII-17 Ph        Ph R.sup.102  = OPh R.sup.106  =                                                OPh H H H                                VII-18 Ph Ph R.sup.102  =            N(C.sub.2 H.sub.5).sub.2 R.sup.106  = N(C.sub.2 H.sub.5).sub.2 H H H                VII-19 Ph Ph R.sup.102  = Cl R.sup.106  =                                  Cl H H H                   VII-20 Ph Ph H H H H R.sup.38  = R.sup.43  =       CH.sub.3                                                                        VII-21 Ph Ph H H H H R.sup.38  = R.sup.43  =                                   OCH.sub.3                   VII-22 Ph Ph H H H H R.sup.38  = R.sup.43         =                                                                               N(CH.sub.3).sub.2                                                             VII-23 Ph Ph H H H H R.sup.38  = R.sup.43  =                                    Cl                                                                                                                        VII-24                              ##STR400##                                                                     ##STR401##                                                                     H H H H H                                                                     VII-25                                                                          ##STR402##                                                                     ##STR403##                                                                     H H H H H                                                                     VII-26                                                                          ##STR404##                                                                     ##STR405##                                                                     H H H H H                                                                     VII-27 Ph                                                                       ##STR406##                                                                     H H H H H                                                                     VII-28                                                                          ##STR407##                                                                     ##STR408##                                                                     H H H H H                                                                     VII-29                                                                          ##STR409##                                                                     ##STR410##                                                                     H H H H H                                                                     VII-30                                                                          ##STR411##                                                                     ##STR412##                                                                     H H H H H                                                                     VII-31                                                                          ##STR413##                                                                     ##STR414##                                                                     H H H H H                                                                     VII-32                                                                          ##STR415##                                                                     ##STR416##                                                                     H H H H H                                                                     VII-33                                                                          ##STR417##                                                                     ##STR418##                                                                     H H H H H                                                                     VII-34                                                                          ##STR419##                                                                     ##STR420##                                                                     H H H H H                                                                     VII-35                                                                          ##STR421##                                                                     ##STR422##                                                                     H H H H H                                                                     VII-36                                                                          ##STR423##                                                                     ##STR424##                                                                     H H H H H                                                                     VII-37                                                                          ##STR425##                                                                     ##STR426##                                                                     H H H H H                                                                     VII-38                                                                          ##STR427##                                                                     ##STR428##                                                                     H H H H H                                                                      VII-39                                                                         ##STR429##                                                                     ##STR430##                                                                     H H H H H                                                                      VII-40                                                                         ##STR431##                                                                     ##STR432##                                                                     H H H H H                                                                     VII-41                                                                          ##STR433##                                                                     ##STR434##                                                                     H H H H H                                                                      VII-42                                                                         ##STR435##                                                                     ##STR436##                                                                     H H H H H                                                                     VII-43                                                                          ##STR437##                                                                     ##STR438##                                                                     H H H H H                                                                     VII-44                                                                          ##STR439##                                                                     ##STR440##                                                                     H H H H H                                                                      VII-45                                                                         ##STR441##                                                                     ##STR442##                                                                     H H H H H                                                                     VII-46                                                                          ##STR443##                                                                     ##STR444##                                                                     H H H H H                                                                

    TABLE 7                                                                          - Compound                                                                     No. Ar.sub.1 Ar.sub.2 R.sup.101 ˜R.sup.104 R.sup.105                     ˜R.sup.108 R.sup.109 ˜R.sup.113 R.sup.114 ˜R.sup.118        R.sup.37                                                                        ˜R.sup.44                                                                      VII-1 Ph Ph H H H H H                                                    VII-2 Ph Ph H H R.sup.110  = CH.sub.3 R.sup.115  =                             CH.sub.3 H            VII-3 Ph Ph H H R.sup.111  = CH.sub.3 R.sup.116         =                                                                               CH.sub.3 H                                                                    VII-4 Ph Ph H H R.sup.110  = t-C.sub.4 H.sub.9 R.sup.115  = t-C.sub.4          H.sub.9 H                                                                       VII-5 Ph Ph H H R.sup.110  = OCH.sub.3 R.sup.115  = OCH.sub.3 H                        VII-6 Ph Ph H H R.sup.111  = Ph R.sup.115  =                           H H                 VII-7 Ph Ph H H                                            ##STR445##                                                                     ##STR446##                                                                     H                                                                             VII-8 Ph Ph H H R.sup.110  = OPh R.sup.115  =                                   OPh H                       VII-9 Ph Ph H H R.sup.110  = N(C.sub.2            H.sub.5).sub.2 R.sup.115  = N(C.sub.2                                           H.sub.5).sub.2 H                    VII-10 Ph Ph H H R.sup.110  =             N(Ph).sub.2 R.sup.115  =                                                        N(Ph).sub.2 H                                    VII-11 Ph Ph H H             R.sup.110  = Cl R.sup.115  =                                                    Cl H                                         VII-12 Ph Ph R.sup.102  =        CH.sub.3 R.sup.106  =                                                           CH.sub.3 H H H                                      VII-13 Ph Ph H H          R.sup.111  = CH.sub.3 R.sup.115  =                                              CH.sub.3 H                             VII-14 Ph Ph H H R.sup.111  =          OCH.sub.3 R.sup.115  =                                                          OCH.sub.3 H                                        VII-15 Ph Ph               R.sup.102  = OCH.sub.3 R.sup.106  =                                             OCH.sub.3 H H H                       VII-16 Ph Ph R.sup.102  = Ph            R.sup.106  =                                                                    Ph H H H                                                     VII-17 Ph        Ph R.sup.102  = OPh R.sup.106  =                                                OPh H H H                                VII-18 Ph Ph R.sup.102  =            N(C.sub.2 H.sub.5).sub.2 R.sup.106  = N(C.sub.2 H.sub.5).sub.2 H H H                VII-19 Ph Ph R.sup.102  = Cl R.sup.106  =                                  Cl H H H                   VII-20 Ph Ph H H H H R.sup.38  = R.sup.43  =       CH.sub.3                                                                        VII-21 Ph Ph H H H H R.sup.38  = R.sup.43  =                                   OCH.sub.3                   VII-22 Ph Ph H H H H R.sup.38  = R.sup.43         =                                                                               N(CH.sub.3).sub.2                                                             VII-23 Ph Ph H H H H R.sup.38  = R.sup.43  =                                    Cl                                                                                                                        VII-24                              ##STR447##                                                                     ##STR448##                                                                     H H H H H                                                                     VII-25                                                                          ##STR449##                                                                     ##STR450##                                                                     H H H H H                                                                     VII-26                                                                          ##STR451##                                                                     ##STR452##                                                                     H H H H H                                                                     VII-27 Ph                                                                       ##STR453##                                                                     H H H H H                                                                     VII-28                                                                          ##STR454##                                                                     ##STR455##                                                                     H H H H H                                                                     VII-29                                                                          ##STR456##                                                                     ##STR457##                                                                     H H H H H                                                                     VII-30                                                                          ##STR458##                                                                     ##STR459##                                                                     H H H H H                                                                     VII-31                                                                          ##STR460##                                                                     ##STR461##                                                                     H H H H H                                                                     VII-32                                                                          ##STR462##                                                                     ##STR463##                                                                     H H H H H                                                                     VII-33                                                                          ##STR464##                                                                     ##STR465##                                                                     H H H H H                                                                     VII-34                                                                          ##STR466##                                                                     ##STR467##                                                                     H H H H H                                                                     VII-35                                                                          ##STR468##                                                                     ##STR469##                                                                     H H H H H                                                                     VII-36                                                                          ##STR470##                                                                     ##STR471##                                                                     H H H H H                                                                     VII-37                                                                          ##STR472##                                                                     ##STR473##                                                                     H H H H H                                                                     VII-38                                                                          ##STR474##                                                                     ##STR475##                                                                     H H H H H                                                                     VII-39                                                                          ##STR476##                                                                     ##STR477##                                                                     H H H H H                                                                     VII-40                                                                          ##STR478##                                                                     ##STR479##                                                                     H H H H H                                                                     VII-41                                                                          ##STR480##                                                                     ##STR481##                                                                     H H H H H                                                                     VII-42                                                                          ##STR482##                                                                     ##STR483##                                                                     H H H H H                                                                     VII-43                                                                          ##STR484##                                                                     ##STR485##                                                                     H H H H H                                                                     VII-44                                                                          ##STR486##                                                                     ##STR487##                                                                     H H H H H                                                                     VII-45                                                                          ##STR488##                                                                     ##STR489##                                                                     H H H H H                                                                     VII-46                                                                          ##STR490##                                                                     ##STR491##                                                                     H H H H H                                                                

    TABLE 8                                                                          -                                                                              ##STR492##                                                                     Compound No. Ar.sub.1 Ar.sub.3 R.sup.101 ˜R.sup.104 R.sup.119           ˜R.sup.123 R.sup.124 ˜R.sup.127 R.sup.114 ˜R.sup.118         R.sup.37                                                                        ˜R.sup.44                                                                      VIII-1 Ph Ph H H H H H                                                   VIII-2 Ph Ph H H H H R.sup.37 = R.sup.42 =                                     Cl                            VIII-3 Ph Ph H H H H R.sup.38 = R.sup.43        =                                                                               CH.sub.3                                                                      VIII-4 Ph Ph H H H H R.sup.38 = R.sup.43 =                                      OCH.sub.3                      VIII-5 Ph Ph H H H H R.sup.38 = R.sup.43       =                                                                               N(CH.sub.3).sub.2                                                             VIII-6 Ph Ph H R.sup.122 = OCH.sub.3 H R.sup.115 =                              OCH.sub.3 H                                                                                                                     VIII-7 Ph Ph H                ##STR493##                                                                     H                                                                              ##STR494##                                                                     H                                                                             VIII-8 Ph Ph H R.sup.122 = OPh H R.sup.115 =                                    OPh H                        VIII-9 Ph Ph H R.sup.122 = N(C.sub.2             H.sub.5).sub.2 H R.sup.115 = N(C.sub.2                                          H.sub.5).sub.2 H                   VIII-10 Ph Ph H R.sup.122 =                 N(Ph).sub.2 H R.sup.115 =                                                      N(Ph).sub.2 H                                  VIII-11 Ph Ph H R.sup.122       = Cl H R.sup.115 =                                                             Cl H                                                  VIII-12 Ph Ph H         R.sup.122 = t-C.sub.4 H.sub.9 H R.sup.115 = t-C.sub.4                           H.sub.9 H           VIII-13 Ph Ph H R.sup.122 = CH.sub.3 H R.sup.115 =        CH.sub.3 H                                                                      VIII-14 Ph Ph H R.sup.121 = CH.sub.3 H R.sup.116 =                             CH.sub.3 H            VIII-15 Ph Ph H R.sup.121 =                              Ph H H H               VIII-16 Ph Ph R.sup.102 = CH.sub.3 H R.sup.126 =       CH.sub.3 H H                                                                    VIII-17 Ph Ph R.sup.102 = OCH.sub.3 H R.sup.126 = OCH.sub.3 H H                        VIII-18 Ph Ph R.sup.102 = Ph H R.sup.126 =                             Ph H H                VIII-19 Ph Ph R.sup.102 = OPh H R.sup.126 = OPh H       H                                                                               VIII-20 Ph Ph R.sup.102 = N(C.sub.2 H.sub.5).sub.2 H R.sup.126 =              N(C.sub.2                                                                       H.sub.5).sub.2 H H                                              VIII-21       Ph Ph R.sup.102 = Cl H R.sup.126 =                                              Cl H H                                                                                                          VIII-22                                       ##STR495##                                                                     ##STR496##                                                                     H H H H H                                                                     VIII-23                                                                         ##STR497##                                                                     ##STR498##                                                                     H H H H H                                                                     VIII-24                                                                         ##STR499##                                                                     ##STR500##                                                                     H H H H H                                                                     VIII-25                                                                         ##STR501##                                                                     ##STR502##                                                                     H H H H H                                                                      VIII-26                                                                        ##STR503##                                                                     ##STR504##                                                                     H H H H H                                                                     VIII-27                                                                         ##STR505##                                                                     ##STR506##                                                                     H H H H H                                                                     VIII-28                                                                         ##STR507##                                                                     ##STR508##                                                                     H H H H H                                                                      VIII-29                                                                        ##STR509##                                                                     ##STR510##                                                                     H H H H H                                                                     VIII-30                                                                         ##STR511##                                                                     ##STR512##                                                                     H H H H H                                                                     VIII-31                                                                         ##STR513##                                                                     ##STR514##                                                                     H H H H H                                                                     VIII-32                                                                         ##STR515##                                                                     ##STR516##                                                                     H H H H H                                                                      VIII-33                                                                        ##STR517##                                                                     ##STR518##                                                                     H H H H H                                                                     VIII-34                                                                         ##STR519##                                                                     ##STR520##                                                                     H H H H H                                                                      VIII-35                                                                        ##STR521##                                                                     ##STR522##                                                                     H H H H H                                                                     VIII-36 Ph Ph H H H H R.sup.37 = R.sup.42 =                                     CH.sub.3                                                                                                                 VIII-37                              ##STR523##                                                                     ##STR524##                                                                     H H H H H                                                                      VIII-38                                                                        ##STR525##                                                                     ##STR526##                                                                     H H H H H                                                                     VIII-39                                                                         ##STR527##                                                                     ##STR528##                                                                     H H H H H                                                                     VIII-40                                                                         ##STR529##                                                                     ##STR530##                                                                     H H H H H                                                                     VIII-41                                                                         ##STR531##                                                                     ##STR532##                                                                     H H H H H                                                                     VIII-42                                                                         ##STR533##                                                                     ##STR534##                                                                     H H H H H                                                                      VIII-43                                                                        ##STR535##                                                                     ##STR536##                                                                     H H H H H                                                                      VIII-44                                                                        ##STR537##                                                                     ##STR538##                                                                     H H H H H                                                                

    TABLE 8                                                                          - Compound No. Ar.sub.1 Ar.sub.3 R.sup.101 ˜R.sup.104 R.sup.119         ˜R.sup.123 R.sup.124 ˜R.sup.127 R.sup.114 ˜R.sup.118         R.sup.37                                                                        ˜R.sup.44                                                                      VIII-1 Ph Ph H H H H H                                                   VIII-2 Ph Ph H H H H R.sup.37 = R.sup.42 =                                     Cl                            VIII-3 Ph Ph H H H H R.sup.38 = R.sup.43        =                                                                               CH.sub.3                                                                      VIII-4 Ph Ph H H H H R.sup.38 = R.sup.43 =                                      OCH.sub.3                      VIII-5 Ph Ph H H H H R.sup.38 = R.sup.43       =                                                                               N(CH.sub.3).sub.2                                                             VIII-6 Ph Ph H R.sup.122 = OCH.sub.3 H R.sup.115 =                              OCH.sub.3 H                                                                                                                     VIII-7 Ph Ph H                ##STR539##                                                                     H                                                                              ##STR540##                                                                     H                                                                             VIII-8 Ph Ph H R.sup.122 = OPh H R.sup.115 =                                    OPh H                        VIII-9 Ph Ph H R.sup.122 = N(C.sub.2             H.sub.5).sub.2 H R.sup.115 = N(C.sub.2                                          H.sub.5).sub.2 H                   VIII-10 Ph Ph H R.sup.122 =                 N(Ph).sub.2 H R.sup.115 =                                                      N(Ph).sub.2 H                                  VIII-11 Ph Ph H R.sup.122       = Cl H R.sup.115 =                                                             Cl H                                                  VIII-12 Ph Ph H         R.sup.122 = t-C.sub.4 H.sub.9 H R.sup.115 = t-C.sub.4                           H.sub.9 H           VIII-13 Ph Ph H R.sup.122 = CH.sub.3 H R.sup.115 =        CH.sub.3 H                                                                      VIII-14 Ph Ph H R.sup.121 = CH.sub.3 H R.sup.116 =                             CH.sub.3 H            VIII-15 Ph Ph H R.sup.121 =                              Ph H H H               VIII-16 Ph Ph R.sup.102 = CH.sub.3 H R.sup.126 =       CH.sub.3 H H                                                                    VIII-17 Ph Ph R.sup.102 = OCH.sub.3 H R.sup.126 = OCH.sub.3 H H                        VIII-18 Ph Ph R.sup.102 = Ph H R.sup.126 =                             Ph H H                VIII-19 Ph Ph R.sup.102 = OPh H R.sup.126 = OPh H       H                                                                               VIII-20 Ph Ph R.sup.102 = N(C.sub.2 H.sub.5).sub.2 H R.sup.126 =              N(C.sub.2                                                                       H.sub.5).sub.2 H H                                              VIII-21       Ph Ph R.sup.102 = Cl H R.sup.126 =                                              Cl H H                                                                                                          VIII-22                                       ##STR541##                                                                     ##STR542##                                                                     H H H H H                                                                     VIII-23                                                                         ##STR543##                                                                     ##STR544##                                                                     H H H H H                                                                     VIII-24                                                                         ##STR545##                                                                     ##STR546##                                                                     H H H H H                                                                     VIII-25                                                                         ##STR547##                                                                     ##STR548##                                                                     H H H H H                                                                     VIII-26                                                                         ##STR549##                                                                     ##STR550##                                                                     H H H H H                                                                     VIII-27                                                                         ##STR551##                                                                     ##STR552##                                                                     H H H H H                                                                     VIII-28                                                                         ##STR553##                                                                     ##STR554##                                                                     H H H H H                                                                     VIII-29                                                                         ##STR555##                                                                     ##STR556##                                                                     H H H H H                                                                     VIII-30                                                                         ##STR557##                                                                     ##STR558##                                                                     H H H H H                                                                     VIII-31                                                                         ##STR559##                                                                     ##STR560##                                                                     H H H H H                                                                     VIII-32                                                                         ##STR561##                                                                     ##STR562##                                                                     H H H H H                                                                     VIII-33                                                                         ##STR563##                                                                     ##STR564##                                                                     H H H H H                                                                     VIII-34                                                                         ##STR565##                                                                     ##STR566##                                                                     H H H H H                                                                     VIII-35                                                                         ##STR567##                                                                     ##STR568##                                                                     H H H H H                                                                     VIII-36 Ph Ph H H H H R.sup.37 = R.sup.42 =                                     CH.sub.3                                                                                                                 VIII-37                              ##STR569##                                                                     ##STR570##                                                                     H H H H H                                                                     VIII-38                                                                         ##STR571##                                                                     ##STR572##                                                                     H H H H H                                                                     VIII-39                                                                         ##STR573##                                                                     ##STR574##                                                                     H H H H H                                                                     VIII-40                                                                         ##STR575##                                                                     ##STR576##                                                                     H H H H H                                                                     VIII-41                                                                         ##STR577##                                                                     ##STR578##                                                                     H H H H H                                                                     VIII-42                                                                         ##STR579##                                                                     ##STR580##                                                                     H H H H H                                                                     VIII-43                                                                         ##STR581##                                                                     ##STR582##                                                                     H H H H H                                                                     VIII-44                                                                         ##STR583##                                                                     ##STR584##                                                                     H H H H H                                                                

    TABLE 9                                                                          -                                                                              ##STR585##                                                                     Compound                                                                       No. Ar.sub.1 Ar.sub.2 Ar.sub.3 R.sup.101 ˜R.sup.104 R.sup.105           ˜R.sup.108 R.sup.124 ˜R.sup.127 R.sup.114                           ˜R.sup.118                                                                       R.sup.37                                                               ˜R.sup.34                                         IX-1 Ph Ph Ph H       H H H H                                                                         IX-2 Ph Ph Ph H H H R.sup.116 = CH.sub.3 R.sup.37 = R.sup.43 = CH.sub.3        IX-3 Ph Ph Ph H H H H R.sup.38 = R.sup.43 =                                    OCH.sub.3                    IX-4 Ph Ph Ph H H H H R.sup.38 = R.sup.43        =                                                                                       N(CH.sub.3).sub.2                                                      IX-5 Ph Ph Ph H H H H R.sup.38 = R.sup.43 =                                    Cl                           IX-6 Ph Ph Ph H H H R.sup.115 = CH.sub.3 H        IX-7 Ph Ph Ph H H H R.sup.115 = t-C.sub.4                                      H.sub.9 H                      IX-8 Ph Ph Ph H H H R.sup.115 =                 OCH.sub.3 H                                                                   IX-9 Ph Ph Ph H H H                                                             ##STR586##                                                                     H                                                                             IX-10 Ph Ph Ph H H H R.sup.115 =                                                OPh H                                    IX-11 Ph Ph Ph H H H R.sup.115       = N(C.sub.2                                                                     H.sub.5).sub.2 H                                              IX-12 Ph        Ph Ph H H H R.sup.115 =                                                         N(Ph).sub.2 H                                     IX-13 Ph Ph Ph H H H        R.sup.115 =                                                                     Cl H                                                          IX-14 Ph        Ph Ph R.sup.102 = CH.sub.3 R.sup.106 = CH.sub.3 R.sup.126 = CH.sub.3 H H        IX-15 Ph Ph Ph R.sup.102 = OCH.sub.3 R.sup.106 = OCH.sub.3 R.sup.126 =        OCH.sub.3 H H                                                                           R.sup.37                                                               ˜R.sup.44                                         IX-16 Ph Ph Ph        R.sup.102 = Ph R.sup.106 = Ph R.sup.126 =                                       Ph H H                          IX-17 Ph Ph Ph R.sup.102 =                     OPh R.sup.106 = OPh R.sup.126 =                                                OPh H H                                  IX-18 Ph Ph Ph R.sup.102 =           N(C.sub.2 H.sub.5).sub.2 R.sup.106 = N(C.sub.2 H.sub.5).sub.2 R.sup.126        = N(C.sub.2                                                                     H.sub.5).sub.2 H H                                            IX-19 Ph        Ph Ph R.sup.102 = Cl R.sup.106 = Cl R.sup.126 =                                 Cl H H                                                                                                                       IX-20                            ##STR587##                                                                     ##STR588##                                                                     ##STR589##                                                                     H H H H H                                                                     IX-21                                                                           ##STR590##                                                                     ##STR591##                                                                     ##STR592##                                                                     H H H H H                                                                     IX-22                                                                           ##STR593##                                                                     ##STR594##                                                                     ##STR595##                                                                     H H H H H                                                                     IX-23                                                                           ##STR596##                                                                     ##STR597##                                                                     ##STR598##                                                                     H H H H H                                                                     IX-24                                                                           ##STR599##                                                                     ##STR600##                                                                     ##STR601##                                                                     H H H H H                                                                     IX-25                                                                           ##STR602##                                                                     ##STR603##                                                                     ##STR604##                                                                     H H H H H                                                                     IX-26                                                                           ##STR605##                                                                     ##STR606##                                                                     ##STR607##                                                                     H H H H H                                                                     IX-27                                                                           ##STR608##                                                                     ##STR609##                                                                     ##STR610##                                                                     H H H H H                                                                     IX-28                                                                           ##STR611##                                                                     ##STR612##                                                                     ##STR613##                                                                     H H H H H                                                                     IX-29                                                                           ##STR614##                                                                     ##STR615##                                                                     ##STR616##                                                                     H H H H H                                                                     IX-30                                                                           ##STR617##                                                                     ##STR618##                                                                     ##STR619##                                                                     H H H H H                                                                     IX-31                                                                           ##STR620##                                                                     ##STR621##                                                                     ##STR622##                                                                     H H H H H                                                                     IX-32                                                                           ##STR623##                                                                     ##STR624##                                                                     Ph H H H H H                                                                  IX-33                                                                           ##STR625##                                                                     Ph Ph H H H H H                                                               IX-34 Ph                                                                        ##STR626##                                                                     ##STR627##                                                                     H H H H H                                                                     IX-35                                                                           ##STR628##                                                                     Ph Ph H H H H H                                                               IX-36 Ph                                                                        ##STR629##                                                                     ##STR630##                                                                     H H H H H                                                                     IX-37                                                                           ##STR631##                                                                     ##STR632##                                                                     Ph H H H H H                                                                  IX-38                                                                           ##STR633##                                                                     Ph                                                                             ##STR634##                                                                     H H H H H                                                                     IX-39                                                                           ##STR635##                                                                     ##STR636##                                                                     Ph H H H H H                                                                  IX-40                                                                           ##STR637##                                                                     Ph Ph H H H H H                                                               IX-41                                                                           ##STR638##                                                                     Ph Ph H H H H H                                                               IX-42                                                                           ##STR639##                                                                     Ph Ph H H H H H                                                               IX-43                                                                           ##STR640##                                                                     Ph Ph H H H H H                                                               IX-44                                                                           ##STR641##                                                                     Ph Ph H H H H H                                                               IX-45                                                                           ##STR642##                                                                     Ph Ph H H H H H                                                               IX-46                                                                           ##STR643##                                                                     Ph Ph H H H H H                                                               IX-47                                                                           ##STR644##                                                                     Ph Ph H H H H H                                                          

    TABLE 9                                                                          - Compound                                                                     No. Ar.sub.1 Ar.sub.2 Ar.sub.3 R.sup.101 ˜R.sup.104 R.sup.105           ˜R.sup.108 R.sup.124 ˜R.sup.127 R.sup.114                           ˜R.sup.118                                                                       R.sup.37                                                               ˜R.sup.34                                         IX-1 Ph Ph Ph H       H H H H                                                                         IX-2 Ph Ph Ph H H H R.sup.116 = CH.sub.3 R.sup.37 = R.sup.43 = CH.sub.3        IX-3 Ph Ph Ph H H H H R.sup.38 = R.sup.43 =                                    OCH.sub.3                    IX-4 Ph Ph Ph H H H H R.sup.38 = R.sup.43        =                                                                                       N(CH.sub.3).sub.2                                                      IX-5 Ph Ph Ph H H H H R.sup.38 = R.sup.43 =                                    Cl                           IX-6 Ph Ph Ph H H H R.sup.115 = CH.sub.3 H        IX-7 Ph Ph Ph H H H R.sup.115 = t-C.sub.4                                      H.sub.9 H                      IX-8 Ph Ph Ph H H H R.sup.115 =                 OCH.sub.3 H                                                                   IX-9 Ph Ph Ph H H H                                                             ##STR645##                                                                     H                                                                             IX-10 Ph Ph Ph H H H R.sup.115 =                                                OPh H                                    IX-11 Ph Ph Ph H H H R.sup.115       = N(C.sub.2                                                                     H.sub.5).sub.2 H                                              IX-12 Ph        Ph Ph H H H R.sup.115 =                                                         N(Ph).sub.2 H                                     IX-13 Ph Ph Ph H H H        R.sup.115 =                                                                     Cl H                                                          IX-14 Ph        Ph Ph R.sup.102 = CH.sub.3 R.sup.106 = CH.sub.3 R.sup.126 = CH.sub.3 H H        IX-15 Ph Ph Ph R.sup.102 = OCH.sub.3 R.sup.106 = OCH.sub.3 R.sup.126 =        OCH.sub.3 H H                                                                           R.sup.37                                                               ˜R.sup.44                                         IX-16 Ph Ph Ph        R.sup.102 = Ph R.sup.106 = Ph R.sup.126 =                                       Ph H H                          IX-17 Ph Ph Ph R.sup.102 =                     OPh R.sup.106 = OPh R.sup.126 =                                                OPh H H                                  IX-18 Ph Ph Ph R.sup.102 =           N(C.sub.2 H.sub.5).sub.2 R.sup.106 = N(C.sub.2 H.sub.5).sub.2 R.sup.126        = N(C.sub.2                                                                     H.sub.5).sub.2 H H                                            IX-19 Ph        Ph Ph R.sup.102 = Cl R.sup.106 = Cl R.sup.126 =                                 Cl H H                                                                                                                       IX-20                            ##STR646##                                                                     ##STR647##                                                                     ##STR648##                                                                     H H H H H                                                                     IX-21                                                                           ##STR649##                                                                     ##STR650##                                                                     ##STR651##                                                                     H H H H H                                                                     IX-22                                                                           ##STR652##                                                                     ##STR653##                                                                     ##STR654##                                                                     H H H H H                                                                     IX-23                                                                           ##STR655##                                                                     ##STR656##                                                                     ##STR657##                                                                     H H H H H                                                                     IX-24                                                                           ##STR658##                                                                     ##STR659##                                                                     ##STR660##                                                                     H H H H H                                                                     IX-25                                                                           ##STR661##                                                                     ##STR662##                                                                     ##STR663##                                                                     H H H H H                                                                     IX-26                                                                           ##STR664##                                                                     ##STR665##                                                                     ##STR666##                                                                     H H H H H                                                                     IX-27                                                                           ##STR667##                                                                     ##STR668##                                                                     ##STR669##                                                                     H H H H H                                                                     IX-28                                                                           ##STR670##                                                                     ##STR671##                                                                     ##STR672##                                                                     H H H H H                                                                     IX-29                                                                           ##STR673##                                                                     ##STR674##                                                                     ##STR675##                                                                     H H H H H                                                                     IX-30                                                                           ##STR676##                                                                     ##STR677##                                                                     ##STR678##                                                                     H H H H H                                                                     IX-31                                                                           ##STR679##                                                                     ##STR680##                                                                     ##STR681##                                                                     H H H H H                                                                     IX-32                                                                           ##STR682##                                                                     ##STR683##                                                                     Ph H H H H H                                                                  IX-33                                                                           ##STR684##                                                                     Ph Ph H H H H H                                                               IX-34 Ph                                                                        ##STR685##                                                                     ##STR686##                                                                     H H H H H                                                                     IX-35                                                                           ##STR687##                                                                     Ph Ph H H H H H                                                               IX-36 Ph                                                                        ##STR688##                                                                     ##STR689##                                                                     H H H H H                                                                     IX-37                                                                           ##STR690##                                                                     ##STR691##                                                                     Ph H H H H H                                                                  IX-38                                                                           ##STR692##                                                                     Ph                                                                             ##STR693##                                                                     H H H H H                                                                     IX-39                                                                           ##STR694##                                                                     ##STR695##                                                                     Ph H H H H H                                                                  IX-40                                                                           ##STR696##                                                                     Ph Ph H H H H H                                                               IX-41                                                                           ##STR697##                                                                     Ph Ph H H H H H                                                               IX-42                                                                           ##STR698##                                                                     Ph Ph H H H H H                                                               IX-43                                                                           ##STR699##                                                                     Ph Ph H H H H H                                                               IX-44                                                                           ##STR700##                                                                     Ph Ph H H H H H                                                               IX-45                                                                           ##STR701##                                                                     Ph Ph H H H H H                                                               IX-46                                                                           ##STR702##                                                                     Ph Ph H H H H H                                                               IX-47                                                                           ##STR703##                                                                     Ph Ph H H H H H                                                          

    TABLE 10                                                                         -                                                                              ##STR704##                                                                     Compound No. Ar.sub.4 Ar.sub.5 R.sup.201 ˜R.sup.204 R.sup.205           ˜R.sup.208 R.sup.209 ˜R.sup.213 R.sup.214 ˜R.sup.218         R.sup.37                                                                        ˜R.sup.44                                                                      X-1 Ph Ph H H H H H                                                     X-2                                                                             ##STR705##                                                                     ##STR706##                                                                     H H H H H                                                                      X-3                                                                            ##STR707##                                                                     ##STR708##                                                                     H H H H H                                                                     X-4                                                                             ##STR709##                                                                     ##STR710##                                                                     H H H H H                                                                      X-5                                                                            ##STR711##                                                                     ##STR712##                                                                     H H H H H                                                                     X-6                                                                             ##STR713##                                                                     ##STR714##                                                                     H H H H H                                                                      X-7                                                                            ##STR715##                                                                     ##STR716##                                                                     H H H H H                                                                     X-8                                                                             ##STR717##                                                                     ##STR718##                                                                     H H H H H                                                                     X-9                                                                             ##STR719##                                                                     ##STR720##                                                                     H H H H H                                                                     X-10                                                                            ##STR721##                                                                     ##STR722##                                                                     H H H H H                                                                      X-11                                                                           ##STR723##                                                                     ##STR724##                                                                     H H H H H                                                                     X-12                                                                            ##STR725##                                                                     ##STR726##                                                                     H H H H H                                                                     X-13                                                                            ##STR727##                                                                     ##STR728##                                                                     H H H H H                                                                      X-14                                                                           ##STR729##                                                                     ##STR730##                                                                     H H H H H                                                                     X-15                                                                            ##STR731##                                                                     ##STR732##                                                                     H H H H H                                                                      X-16                                                                           ##STR733##                                                                     ##STR734##                                                                     H H H H H                                                                     X-17                                                                            ##STR735##                                                                     ##STR736##                                                                     H H H H H                                                                      X-18                                                                           ##STR737##                                                                     ##STR738##                                                                     H H H H R.sup.37 = R.sup.42 =                                                  CH.sub.3                                                                                                    X-19                                              ##STR739##                                                                     ##STR740##                                                                     H H H H R.sup.37 = R.sup.42 =                                                  CH.sub.3                                                                                                    X-20                                              ##STR741##                                                                     ##STR742##                                                                     H H H H H                                                                     X-21                                                                            ##STR743##                                                                     ##STR744##                                                                     H H H H H                                                                      X-22                                                                           ##STR745##                                                                     ##STR746##                                                                     H H H H H                                                                     X-23                                                                            ##STR747##                                                                     ##STR748##                                                                     H H H H H                                                                      X-24                                                                           ##STR749##                                                                     ##STR750##                                                                     H H H H H                                                                      X-25 Ph Ph H H R.sup.210 = CH.sub.3 R.sup.215 =                                CH.sub.3 H               X-26 Ph Ph H H R.sup.211 = CH.sub.3 R.sup.216        =                                                                               CH.sub.3 H                                                                    X-27 Ph Ph H H R.sup.211 = t-C.sub.4 H.sub.9 R.sup.216 = t-C.sub.4             H.sub.9 H                                                                       X-28 Ph Ph H H R.sup.211 = OCH.sub.3 R.sup.216 =                               OCH.sub.3 H             X-29 Ph Ph H H R.sup.211 =                             Ph H H                X-30 Ph Ph H H                                           ##STR751##                                                                     ##STR752##                                                                     H                                                                              X-31 Ph Ph H H R.sup.211 = OPh R.sup.216 =                                     OPh H                         X-32 Ph Ph H H R.sup.211 = N(C.sub.2            H.sub.5).sub.2 R.sup.216 = N(C.sub.2                                            H.sub.5).sub.2 H                     X-33 Ph Ph H H R.sup.211 =               N(Ph).sub.2 R.sup.216 =                                                         N(Ph).sub.2 H                                     X-34 Ph Ph H H              R.sup.211 = Cl R.sup.216 =                                                      Cl H                                           X-35 Ph Ph H H R.sup.211       = CH.sub.3 R.sup.215 =                                                          CH.sub.3 H                                         X-36 Ph Ph H H H H         R.sup.38 = R.sup.43 =                                                           CH.sub.3                                            X-37 Ph Ph H H H H        R.sup.38 = R.sup.43 =                                                           OCH.sub.3                                           X-38 Ph Ph H H H H        R.sup.38 = R.sup.43 =                                                           N(CH.sub.3).sub.2                                   X-39 Ph Ph H H H H        R.sup.38 = R.sup.43 =                                                           Cl                                                  X-40 Ph Ph H H H H        R.sup.37 = R.sup.42 =                                                           CH.sub.3                                            X-41                       ##STR753##                                                                     ##STR754##                                                                     H H H H H                                                                     X-42                                                                            ##STR755##                                                                     ##STR756##                                                                     H H H H H                                                                     X-43                                                                            ##STR757##                                                                     ##STR758##                                                                     H H H H H                                                                      X-44                                                                           ##STR759##                                                                     ##STR760##                                                                     H H H H H                                                                      X-45                                                                           ##STR761##                                                                     ##STR762##                                                                     H H H H H                                                                

    TABLE 10                                                                         - Compound No. Ar.sub.4 Ar.sub.5 R.sup.201 ˜R.sup.204 R.sup.205         ˜R.sup.208 R.sup.209 ˜R.sup.213 R.sup.214 ˜R.sup.218         R.sup.37                                                                        ˜R.sup.44                                                                      X-1 Ph Ph H H H H H                                                     X-2                                                                             ##STR763##                                                                     ##STR764##                                                                     H H H H H                                                                     X-3                                                                             ##STR765##                                                                     ##STR766##                                                                     H H H H H                                                                     X-4                                                                             ##STR767##                                                                     ##STR768##                                                                     H H H H H                                                                     X-5                                                                             ##STR769##                                                                     ##STR770##                                                                     H H H H H                                                                     X-6                                                                             ##STR771##                                                                     ##STR772##                                                                     H H H H H                                                                     X-7                                                                             ##STR773##                                                                     ##STR774##                                                                     H H H H H                                                                     X-8                                                                             ##STR775##                                                                     ##STR776##                                                                     H H H H H                                                                     X-9                                                                             ##STR777##                                                                     ##STR778##                                                                     H H H H H                                                                     X-10                                                                            ##STR779##                                                                     ##STR780##                                                                     H H H H H                                                                     X-11                                                                            ##STR781##                                                                     ##STR782##                                                                     H H H H H                                                                     X-12                                                                            ##STR783##                                                                     ##STR784##                                                                     H H H H H                                                                     X-13                                                                            ##STR785##                                                                     ##STR786##                                                                     H H H H H                                                                     X-14                                                                            ##STR787##                                                                     ##STR788##                                                                     H H H H H                                                                     X-15                                                                            ##STR789##                                                                     ##STR790##                                                                     H H H H H                                                                     X-16                                                                            ##STR791##                                                                     ##STR792##                                                                     H H H H H                                                                     X-17                                                                            ##STR793##                                                                     ##STR794##                                                                     H H H H H                                                                     X-18                                                                            ##STR795##                                                                     ##STR796##                                                                     H H H H R.sup.37 = R.sup.42 =                                                  CH.sub.3                                                                                                    X-19                                              ##STR797##                                                                     ##STR798##                                                                     H H H H R.sup.37 = R.sup.42 =                                                  CH.sub.3                                                                                                    X-20                                              ##STR799##                                                                     ##STR800##                                                                     H H H H H                                                                     X-21                                                                            ##STR801##                                                                     ##STR802##                                                                     H H H H H                                                                     X-22                                                                            ##STR803##                                                                     ##STR804##                                                                     H H H H H                                                                     X-23                                                                            ##STR805##                                                                     ##STR806##                                                                     H H H H H                                                                     X-24                                                                            ##STR807##                                                                     ##STR808##                                                                     H H H H H                                                                     X-25 Ph Ph H H R.sup.210 = CH.sub.3 R.sup.215 =                                 CH.sub.3 H                X-26 Ph Ph H H R.sup.211 = CH.sub.3 R.sup.216       =                                                                               CH.sub.3 H                                                                    X-27 Ph Ph H H R.sup.211 = t-C.sub.4 H.sub.9 R.sup.216 = t-C.sub.4             H.sub.9 H                                                                       X-28 Ph Ph H H R.sup.211 = OCH.sub.3 R.sup.216 =                               OCH.sub.3 H             X-29 Ph Ph H H R.sup.211 =                             Ph H H                                                                                                                           X-30 Ph Ph H H               ##STR809##                                                                     ##STR810##                                                                     H                                                                             X-31 Ph Ph H H R.sup.211 = OPh R.sup.216 =                                      OPh H                          X-32 Ph Ph H H R.sup.211 = N(C.sub.2           H.sub.5).sub.2 R.sup.216 = N(C.sub.2                                            H.sub.5).sub.2 H                     X-33 Ph Ph H H R.sup.211 =               N(Ph).sub.2 R.sup.216 =                                                         N(Ph).sub.2 H                                     X-34 Ph Ph H H              R.sup.211 = Cl R.sup.216 =                                                      Cl H                                           X-35 Ph Ph H H R.sup.211       = CH.sub.3 R.sup.215 =                                                          CH.sub.3 H                                         X-36 Ph Ph H H H H         R.sup.38 = R.sup.43 =                                                           CH.sub.3                                            X-37 Ph Ph H H H H        R.sup.38 = R.sup.43 =                                                           OCH.sub.3                                           X-38 Ph Ph H H H H        R.sup.38 = R.sup.43 =                                                           N(CH.sub.3).sub.2                                   X-39 Ph Ph H H H H        R.sup.38 = R.sup.43 =                                                           Cl                                                  X-40 Ph Ph H H H H        R.sup.37 = R.sup.42 =                                                           CH.sub.3                                                                                           X-41                                                       ##STR811##                                                                     ##STR812##                                                                     H H H H H                                                                     X-42                                                                            ##STR813##                                                                     ##STR814##                                                                     H H H H H                                                                     X-43                                                                            ##STR815##                                                                     ##STR816##                                                                     H H H H H                                                                     X-44                                                                            ##STR817##                                                                     ##STR818##                                                                     H H H H H                                                                     X-45                                                                            ##STR819##                                                                     ##STR820##                                                                     H H H H H                                                                

    TABLE 11                                                                         -                                                                              ##STR821##                                                                     Compound No. Ar.sub.4 Ar.sub.6 R.sup.201 ˜R.sup.204 R.sup.219           ˜R.sup.223 R.sup.224 ˜R.sup.227 R.sup.214 ˜R.sup.218         R.sup.37                                                                        ˜R.sup.44                                                                      XI-1 Ph Ph H H H H H                                                     XI-2 Ph Ph H H H H R.sup.37 = R.sup.42 =                                       Cl                              XI-3 Ph Ph H H H H R.sup.37 = R.sup.42        =                                                                               OCH.sub.3                                                                     XI-4 Ph Ph H H H H R.sup.37 = R.sup.42 =                                        CH.sub.3                                                                                                              XI-5                                    ##STR822##                                                                     ##STR823##                                                                     H H H H H                                                                     XI-6                                                                            ##STR824##                                                                     ##STR825##                                                                     H H H H H                                                                     XI-7                                                                            ##STR826##                                                                     ##STR827##                                                                     H H H H H                                                                     XI-8                                                                            ##STR828##                                                                     ##STR829##                                                                     H H H H H                                                                     XI-9                                                                            ##STR830##                                                                     ##STR831##                                                                     H H H H H                                                                     XI-10                                                                           ##STR832##                                                                     ##STR833##                                                                     H H H H H                                                                     XI-11                                                                           ##STR834##                                                                     ##STR835##                                                                     H H H H H                                                                     XI-12                                                                           ##STR836##                                                                     ##STR837##                                                                     H H H H H                                                                     XI-13                                                                           ##STR838##                                                                     ##STR839##                                                                     H H H H H                                                                     XI-14                                                                           ##STR840##                                                                     ##STR841##                                                                     H H H H H                                                                     XI-15                                                                           ##STR842##                                                                     ##STR843##                                                                     H H H H H                                                                     XI-16                                                                           ##STR844##                                                                     ##STR845##                                                                     H H H H H                                                                     XI-17                                                                           ##STR846##                                                                     ##STR847##                                                                     H H H H H                                                                     XI-18                                                                           ##STR848##                                                                     ##STR849##                                                                     H H H H H                                                                     XI-19                                                                           ##STR850##                                                                     ##STR851##                                                                     H H H H H                                                                     XI-20                                                                           ##STR852##                                                                     ##STR853##                                                                     H H H H H                                                                     XI-21                                                                           ##STR854##                                                                     ##STR855##                                                                     H H H H H                                                                     XI-22                                                                           ##STR856##                                                                     ##STR857##                                                                     H H H H H                                                                     XI-23                                                                           ##STR858##                                                                     ##STR859##                                                                     H R.sup.220 = CH.sub.3 H R.sup.215 =                                           CH.sub.3 H                                                                                                         XI-24 Ph Ph H R.sup.220 = CH.sub.3        H R.sup.217 =                                                                   CH.sub.3 H                                                  XI-25 Ph Ph       H R.sup.221 = CH.sub.3 H R.sup.216 =                                            CH.sub.3 H                           XI-26 Ph Ph H R.sup.221 =                 t-C.sub.4 H.sub.9 H R.sup.216 = t-C.sub.4                                      H.sub.9 H                      XI-27 Ph Ph H R.sup.221 = OCH.sub.3 H          R.sup.216 =                                                                     OCH.sub.3 H                                                   XI-28 Ph        Ph H R.sup.221 =                                                                Ph H H H                                                 XI-29 Ph Ph H        R.sup.221 = OPh H R.sup.216 =                                                   OPh H                                       XI-30 Ph Ph H R.sup.221 =         N(C.sub.2 H.sub.5).sub.2 H R.sup.216 = N(C.sub.2 H.sub.5).sub.2 H                      XI-31 Ph Ph H R.sup.221 = N(Ph).sub.2 H R.sup.216 = N(Ph).sub.2        H                                                                               XI-32 Ph Ph H R.sup.221 = Cl H R.sup.216 =                                     Cl H                          XI-33 Ph Ph H R.sup.221 = CH.sub.3 H            R.sup.217 =                                                                     CH.sub.3 H                                                    XI-34 Ph        Ph H H H H R.sup.38 = R.sup.43 =                                                CH.sub.3                                 XI-35 Ph Ph H H H H R.sup.38 =       R.sup.43 =                                                                      OCH.sub.3                                                      XI-36 Ph       Ph H H H H R.sup.38 = R.sup.43 =                                                Cl                                       XI-37 Ph Ph H H H H R.sup.38 =       R.sup.43 =                                                                      N(CH.sub.3).sub.2                                                                      XI-38 Ph Ph H                                                          ##STR860##                                                                     H                                                                              ##STR861##                                                                     H                                                                             XI-39                                                                           ##STR862##                                                                     ##STR863##                                                                     H H H H H                                                                     XI-40                                                                           ##STR864##                                                                     ##STR865##                                                                     H H H H H                                                                     XI-41                                                                           ##STR866##                                                                     ##STR867##                                                                     H H H H H                                                                     XI-42                                                                           ##STR868##                                                                     ##STR869##                                                                     H H H H H                                                                     XI-43                                                                           ##STR870##                                                                     ##STR871##                                                                     H H H H H                                                                

    TABLE 11                                                                         - Compound No. Ar.sub.4 Ar.sub.6 R.sup.201 ˜R.sup.204 R.sup.219         ˜R.sup.223 R.sup.224 ˜R.sup.227 R.sup.214 ˜R.sup.218         R.sup.37                                                                        ˜R.sup.44                                                                      XI-1 Ph Ph H H H H H                                                     XI-2 Ph Ph H H H H R.sup.37 = R.sup.42 =                                       Cl                              XI-3 Ph Ph H H H H R.sup.37 = R.sup.42        =                                                                               OCH.sub.3                                                                     XI-4 Ph Ph H H H H R.sup.37 = R.sup.42 =                                        CH.sub.3                                                                                                              XI-5                                    ##STR872##                                                                     ##STR873##                                                                     H H H H H                                                                     XI-6                                                                            ##STR874##                                                                     ##STR875##                                                                     H H H H H                                                                     XI-7                                                                            ##STR876##                                                                     ##STR877##                                                                     H H H H H                                                                     XI-8                                                                            ##STR878##                                                                     ##STR879##                                                                     H H H H H                                                                     XI-9                                                                            ##STR880##                                                                     ##STR881##                                                                     H H H H H                                                                     XI-10                                                                           ##STR882##                                                                     ##STR883##                                                                     H H H H H                                                                     XI-11                                                                           ##STR884##                                                                     ##STR885##                                                                     H H H H H                                                                     XI-12                                                                           ##STR886##                                                                     ##STR887##                                                                     H H H H H                                                                     XI-13                                                                           ##STR888##                                                                     ##STR889##                                                                     H H H H H                                                                     XI-14                                                                           ##STR890##                                                                     ##STR891##                                                                     H H H H H                                                                     XI-15                                                                           ##STR892##                                                                     ##STR893##                                                                     H H H H H                                                                     XI-16                                                                           ##STR894##                                                                     ##STR895##                                                                     H H H H H                                                                     XI-17                                                                           ##STR896##                                                                     ##STR897##                                                                     H H H H H                                                                     XI-18                                                                           ##STR898##                                                                     ##STR899##                                                                     H H H H H                                                                     XI-19                                                                           ##STR900##                                                                     ##STR901##                                                                     H H H H H                                                                     XI-20                                                                           ##STR902##                                                                     ##STR903##                                                                     H H H H H                                                                     XI-21                                                                           ##STR904##                                                                     ##STR905##                                                                     H H H H H                                                                     XI-22                                                                           ##STR906##                                                                     ##STR907##                                                                     H H H H H                                                                     XI-23                                                                           ##STR908##                                                                     ##STR909##                                                                     H R.sup.220 = CH.sub.3 H R.sup.215 =                                           CH.sub.3 H                                                                                                         XI-24 Ph Ph H R.sup.220 = CH.sub.3        H R.sup.217 =                                                                   CH.sub.3 H                                                  XI-25 Ph Ph       H R.sup.221 = CH.sub.3 H R.sup.216 =                                            CH.sub.3 H                           XI-26 Ph Ph H R.sup.221 =                 t-C.sub.4 H.sub.9 H R.sup.216 = t-C.sub.4                                      H.sub.9 H                      XI-27 Ph Ph H R.sup.221 = OCH.sub.3 H          R.sup.216 =                                                                     OCH.sub.3 H                                                   XI-28 Ph        Ph H R.sup.221 =                                                                Ph H H H                                                 XI-29 Ph Ph H        R.sup.221 = OPh H R.sup.216 =                                                   OPh H                                       XI-30 Ph Ph H R.sup.221 =         N(C.sub.2 H.sub.5).sub.2 H R.sup.216 = N(C.sub.2 H.sub.5).sub.2 H                      XI-31 Ph Ph H R.sup.221 = N(Ph).sub.2 H R.sup.216 = N(Ph).sub.2        H                                                                               XI-32 Ph Ph H R.sup.221 = Cl H R.sup.216 =                                     Cl H                          XI-33 Ph Ph H R.sup.221 = CH.sub.3 H            R.sup.217 =                                                                     CH.sub.3 H                                                    XI-34 Ph        Ph H H H H R.sup.38 = R.sup.43 =                                                CH.sub.3                                 XI-35 Ph Ph H H H H R.sup.38 =       R.sup.43 =                                                                      OCH.sub.3                                                      XI-36 Ph       Ph H H H H R.sup.38 = R.sup.43 =                                                Cl                                       XI-37 Ph Ph H H H H R.sup.38 =       R.sup.43 =                                                                      N(CH.sub.3).sub.2                                                                      XI-38 Ph Ph H                                                          ##STR910##                                                                     H                                                                              ##STR911##                                                                     H                                                                             XI-39                                                                           ##STR912##                                                                     ##STR913##                                                                     H H H H H                                                                     XI-40                                                                           ##STR914##                                                                     ##STR915##                                                                     H H H H H                                                                     XI-41                                                                           ##STR916##                                                                     ##STR917##                                                                     H H H H H                                                                     XI-42                                                                           ##STR918##                                                                     ##STR919##                                                                     H H H H H                                                                     XI-43                                                                           ##STR920##                                                                     ##STR921##                                                                     H H H H H                                                                

    TABLE 12                                                                         -                                                                              ##STR922##                                                                     Compound                                                                       No. Ar.sub.4 Ar.sub.6 Ar.sub.6 R.sup.201 ˜R.sup.204 R.sup.205           ˜R.sup.208 R.sup.224 ˜R.sup.227 R.sup.214 ˜R.sup.218         R.sup.37                                                                        ˜R.sup.44                                                                      XII-1 Ph Ph Ph H H H H H                                                 XII-2 Ph Ph Ph H H H R.sup.215 = CH.sub.3 R.sup.37 = R.sup.42 =               CH.sub.3                                                                        XII-3 Ph Ph Ph H H H R.sup.215 =                                               OCH.sub.3 H                             XII-4 Ph Ph Ph H H H R.sup.215        =                                                                               OPh H                                                                         XII-5 Ph Ph Ph H H H R.sup.215 = Cl R.sup.37 = R.sup.42 =                       Cl                                                                                                                                     XII-6                  ##STR923##                                                                     ##STR924##                                                                     Ph H H H H H                                                                  XII-7                                                                           ##STR925##                                                                     ##STR926##                                                                     Ph H H H H H                                                                  XII-8                                                                           ##STR927##                                                                     ##STR928##                                                                     Ph H H H H H                                                                  XII-9                                                                           ##STR929##                                                                     ##STR930##                                                                     Ph H H H H H                                                                  XII-10                                                                          ##STR931##                                                                     ##STR932##                                                                     Ph H H H H H                                                                  XII-11                                                                          ##STR933##                                                                     ##STR934##                                                                     ##STR935##                                                                     H H H H H                                                                     XII-12                                                                          ##STR936##                                                                     ##STR937##                                                                     ##STR938##                                                                     H H H H H                                                                     XII-13                                                                          ##STR939##                                                                     ##STR940##                                                                     ##STR941##                                                                     H H H H H                                                                     XII-14                                                                          ##STR942##                                                                     ##STR943##                                                                     ##STR944##                                                                     H H H H H                                                                     XII-15                                                                          ##STR945##                                                                     ##STR946##                                                                     Ph H H H H H                                                                  XII-16                                                                          ##STR947##                                                                     ##STR948##                                                                     Ph H H H H H                                                                  XII-17                                                                          ##STR949##                                                                     ##STR950##                                                                     Ph H H H H H                                                                  XII-18                                                                          ##STR951##                                                                     ##STR952##                                                                     Ph H H H H H                                                                  XII-19                                                                          ##STR953##                                                                     ##STR954##                                                                     ##STR955##                                                                     H H H H H                                                                     XII-20                                                                          ##STR956##                                                                     ##STR957##                                                                     ##STR958##                                                                     H H H H H                                                                     XII-21                                                                          ##STR959##                                                                     ##STR960##                                                                     Ph H H H H H                                                                  XII-22                                                                          ##STR961##                                                                     ##STR962##                                                                     ##STR963##                                                                     H H H H H                                                                     XII-23                                                                          ##STR964##                                                                     ##STR965##                                                                     Ph H H H H H                                                                  XII-24                                                                          ##STR966##                                                                     ##STR967##                                                                     ##STR968##                                                                     H H H H H                                                                     XII-25                                                                          ##STR969##                                                                     ##STR970##                                                                     Ph H H H H H                                                                   XII-26                                                                         ##STR971##                                                                     Ph                                                                             ##STR972##                                                                     H H H H H                                                                     XII-27                                                                          ##STR973##                                                                     ##STR974##                                                                     ##STR975##                                                                     H H H H H                                                                      XII-28                                                                         ##STR976##                                                                     ##STR977##                                                                     Ph H H H H H                                                                  XII-29 Ph Ph Ph H H H R.sup.215 =                                               CH.sub.3 H                              XII-30 Ph Ph Ph H H H R.sup.216       =                                                                               CH.sub.3 H                                                                    XII-31 Ph Ph Ph H H H R.sup.216 = t-C.sub.4                                     H.sub.9 H                     XII-32 Ph Ph Ph H H H R.sup.216 =               OCH.sub.3 H                                                                    XII-33 Ph Ph Ph H H H                                                           ##STR978##                                                                     H                                                                              XII-34 Ph Ph Ph H H H R.sup.216 =                                              OPh H                                  XII-35 Ph Ph Ph H H H R.sup.216        = N(C.sub.2                                                                     H.sub.5).sub.2 H                                              XII-36 Ph       Ph Ph H H H R.sup.216 =                                                         N(Ph).sub.2 H                                     XII-37 Ph Ph Ph H H H       R.sup.216 =                                                                     Cl H                                                          XII-38 Ph       Ph Ph H H H H R.sup.38 = R.sup.43 =                                             CH.sub.3                              XII-39 Ph Ph Ph H H H H R.sup.38        = R.sup.43 =                                                                    OCH.sub.3                                                    XII-40 Ph        Ph Ph H H H H R.sup.38 = R.sup.43 =                                             N(CH.sub.3).sub.2                     XII-41 Ph Ph Ph H H H H R.sup.38        = R.sup.43 =                                                                    Cl                                                           XII-42 Ph        Ph Ph H H H H R.sup.37 = R.sup.43 =                                             CH.sub.3                                                                                                             XII-43                                   ##STR979##                                                                     ##STR980##                                                                     Ph H H H H H                                                                  XII-44                                                                          ##STR981##                                                                     ##STR982##                                                                     Ph H H H H H                                                                  XII-45                                                                          ##STR983##                                                                     ##STR984##                                                                     Ph H H H H H                                                                  XII-46                                                                          ##STR985##                                                                     ##STR986##                                                                     Ph H H H H H                                                                  XII-47                                                                          ##STR987##                                                                     ##STR988##                                                                     Ph H H H H H                                                                   XII-48                                                                         ##STR989##                                                                     ##STR990##                                                                     Ph H H H H H                                                             

    TABLE 12                                                                         - Compound                                                                     No. Ar.sub.4 Ar.sub.6 Ar.sub.6 R.sup.201 ˜R.sup.204 R.sup.205           ˜R.sup.208 R.sup.224 ˜R.sup.227 R.sup.214 ˜R.sup.218         R.sup.37                                                                        ˜R.sup.44                                                                      XII-1 Ph Ph Ph H H H H H                                                 XII-2 Ph Ph Ph H H H R.sup.215 = CH.sub.3 R.sup.37 = R.sup.42 =               CH.sub.3                                                                        XII-3 Ph Ph Ph H H H R.sup.215 =                                               OCH.sub.3 H                             XII-4 Ph Ph Ph H H H R.sup.215        =                                                                               OPh H                                                                         XII-5 Ph Ph Ph H H H R.sup.215 = Cl R.sup.37 = R.sup.42 =                       Cl                                                                                                                                     XII-6                  ##STR991##                                                                     ##STR992##                                                                     Ph H H H H H                                                                  XII-7                                                                           ##STR993##                                                                     ##STR994##                                                                     Ph H H H H H                                                                  XII-8                                                                           ##STR995##                                                                     ##STR996##                                                                     Ph H H H H H                                                                  XII-9                                                                           ##STR997##                                                                     ##STR998##                                                                     Ph H H H H H                                                                  XII-10                                                                          ##STR999##                                                                     ##STR1000##                                                                    Ph H H H H H                                                                  XII-11                                                                          ##STR1001##                                                                    ##STR1002##                                                                    ##STR1003##                                                                    H H H H H                                                                     XII-12                                                                          ##STR1004##                                                                    ##STR1005##                                                                    ##STR1006##                                                                    H H H H H                                                                     XII-13                                                                          ##STR1007##                                                                    ##STR1008##                                                                    ##STR1009##                                                                    H H H H H                                                                     XII-14                                                                          ##STR1010##                                                                    ##STR1011##                                                                    ##STR1012##                                                                    H H H H H                                                                     XII-15                                                                          ##STR1013##                                                                    ##STR1014##                                                                    Ph H H H H H                                                                  XII-16                                                                          ##STR1015##                                                                    ##STR1016##                                                                    Ph H H H H H                                                                  XII-17                                                                          ##STR1017##                                                                    ##STR1018##                                                                    Ph H H H H H                                                                  XII-18                                                                          ##STR1019##                                                                    ##STR1020##                                                                    Ph H H H H H                                                                  XII-19                                                                          ##STR1021##                                                                    ##STR1022##                                                                    ##STR1023##                                                                    H H H H H                                                                     XII-20                                                                          ##STR1024##                                                                    ##STR1025##                                                                    ##STR1026##                                                                    H H H H H                                                                     XII-21                                                                          ##STR1027##                                                                    ##STR1028##                                                                    Ph H H H H H                                                                  XII-22                                                                          ##STR1029##                                                                    ##STR1030##                                                                    ##STR1031##                                                                    H H H H H                                                                     XII-23                                                                          ##STR1032##                                                                    ##STR1033##                                                                    Ph H H H H H                                                                  XII-24                                                                          ##STR1034##                                                                    ##STR1035##                                                                    ##STR1036##                                                                    H H H H H                                                                     XII-25                                                                          ##STR1037##                                                                    ##STR1038##                                                                    Ph H H H H H                                                                  XII-26                                                                          ##STR1039##                                                                    Ph                                                                             ##STR1040##                                                                    H H H H H                                                                     XII-27                                                                          ##STR1041##                                                                    ##STR1042##                                                                    ##STR1043##                                                                    H H H H H                                                                     XII-28                                                                          ##STR1044##                                                                    ##STR1045##                                                                    Ph H H H H H                                                                  XII-29 Ph Ph Ph H H H R.sup.215 =                                               CH.sub.3 H                              XII-30 Ph Ph Ph H H H R.sup.216       =                                                                               CH.sub.3 H                                                                    XII-31 Ph Ph Ph H H H R.sup.216 = t-C.sub.4                                     H.sub.9 H                     XII-32 Ph Ph Ph H H H R.sup.216 =               OCH.sub.3 H                                                                    XII-33 Ph Ph Ph H H H                                                           ##STR1046##                                                                    H                                                                             XII-34 Ph Ph Ph H H H R.sup.216 =                                               OPh H                                   XII-35 Ph Ph Ph H H H R.sup.216       = N(C.sub.2                                                                     H.sub.5).sub.2 H                                              XII-36 Ph       Ph Ph H H H R.sup.216 =                                                         N(Ph).sub.2 H                                     XII-37 Ph Ph Ph H H H       R.sup.216 =                                                                     Cl H                                                          XII-38 Ph       Ph Ph H H H H R.sup.38 = R.sup.43 =                                             CH.sub.3                              XII-39 Ph Ph Ph H H H H R.sup.38        = R.sup.43 =                                                                    OCH.sub.3                                                    XII-40 Ph        Ph Ph H H H H R.sup.38 = R.sup.43 =                                             N(CH.sub.3).sub.2                     XII-41 Ph Ph Ph H H H H R.sup.38        = R.sup.43 =                                                                    Cl                                                           XII-42 Ph        Ph Ph H H H H R.sup.37 = R.sup.43 =                                             CH.sub.3                                                                                                         XII-43                                       ##STR1047##                                                                    ##STR1048##                                                                    Ph H H H H H                                                                  XII-44                                                                          ##STR1049##                                                                    ##STR1050##                                                                    Ph H H H H H                                                                  XII-45                                                                          ##STR1051##                                                                    ##STR1052##                                                                    Ph H H H H H                                                                  XII-46                                                                          ##STR1053##                                                                    ##STR1054##                                                                    Ph H H H H H                                                                  XII-47                                                                          ##STR1055##                                                                    ##STR1056##                                                                    Ph H H H H H                                                                  XII-48                                                                          ##STR1057##                                                                    ##STR1058##                                                                    Ph H H H H H                                                                  ##STR1059##                                                               

The inventive compounds can be synthesized by exactly or approximatelythe same method as described in Jean Piccard, Herr. Chim. Acta., 7, 789(1924) and Jean Piccard, J. Am. Chem. Soc., 48, 2878 (1926). Moreparticularly, they can be prepared by effecting Ullman reaction, thatis, by heating a combination of a di(biphenyl)amine compound and adiiodobiphenyl compound, a combination of a N,N'-diphenylbenzidinecompound and iodobiphenyl compound or a similar combination in thepresence of copper. These compounds can be identified by elementalanalysis, infrared absorption spectroscopy (IR), nuclear magneticresonance spectroscopy (proton NMR), etc.

In general, the inventive compounds have a molecular weight of about 640to about 2,000, a high melting point of about 190° to about 300° C., anda high glass transition temperature (Tg) of about 80° to about 200° C.By conventional vacuum deposition or the like, they form a transparent,smooth film of quality which maintains a stable amorphous state evenabove room temperature and over a long period of time. Some of theinventive compounds do not have a melting point and remain amorphous atelevated temperatures. Without a need for binder resin, the inventivecompounds can be formed into a thin film by themselves.

The inventive compounds may be used alone or in admixture of two ormore.

The organic EL element of the invention includes at least one organiccompound layer. The organic compound layer or at least one of organiccompound layers contains the inventive compound. One exemplary structureof the organic EL element according to the present invention is shown inFIG. 1. The EL element generally designated at 1 in FIG. 1 includes on asubstrate 2, an anode 3, a hole injecting and transporting layer 4, alight emitting layer 5, an electron injecting and transporting layer 6,and a cathode 7 stacked in the described order from bottom to top.

The light emitting layer has multi-functions of injecting holes andelectrons, transporting them, and recombining holes and electrons tocreate excitons. A relatively electronically neutral compound ispreferably used in the light emitting layer. The hole injecting andtransporting layer has functions of facilitating injection of holes fromthe anode, transporting them, and obstructing electron transportation.The electron injecting and transporting layer has functions offacilitating injection of electrons from the cathode, transporting them,and obstructing hole transportation. These two layers are effective forincreasing the number of holes and electrons injected into the lightemitting layer and confining holes and electrons therein for optimizingthe recombination region to improve light emission efficiency. Thereforethe hole and electron injecting and transporting layers are optionallyprovided by taking into account the magnitude of the respectivefunctions of the compound used in the light emitting layer for electroninjection and transportation and hole injection and transportation. Forexample, if the compound used in the light emitting layer has anenhanced hole or electron injecting and transporting function, the holeor electron injecting and transporting layer may be omitted because thelight emitting layer itself can also serve as a hole or electroninjecting and transporting layer. In some cases, both the hole andelectron injecting and transporting layers may be omitted. Each of thehole and electron injecting and transporting layers may consist of twosublayers, one sublayer having an injection function and anothersublayer having a transporting function.

The thicknesses of the light admitting layer, hole injecting andtransporting layer, and electron injecting and transporting layer arenot critical and varies with a particular formation technique. Usually asingle layer is about 5 to 1,000 nm thick, especially about 10 to 200nm.

The thicknesses of he hole injecting and transporting layer and electroninjecting and transporting layer are equal to or range from 1/10 to 10times the thickness of the light emitting layer although they depend onthe design of a recombination/light emitting region. When the electronor hole injecting and transporting layer is divided into an injectionlayer and a transporting layer, preferably the injection layer is atleast 1 nm thick and the transporting layer is at least 20 nm thick. Theupper limit of thickness is about 100 nm for the injection layer andabout 1,000 nm for the transporting layer. These film thickness rangesalso apply when two (first and second) injecting and transporting layersare formed.

A freedom of design of the recombination/light emitting region isavailable by controlling the film thicknesses in consideration of thecarrier mobility and carrier density (which is dependent on ionizationpotential and electron affinity) of the light emitting layer, holeinjecting and transporting layer, and electron injecting andtransporting layer to be combined. This enables free design of luminouscolor, control of the luminance and spectrum of light emission by theinterference of the electrodes, and control of the space distribution oflight emission.

The inventive compound is applicable to either a light emitting layer ora hole injecting and transporting layer. Preferably the inventivecompound is used in a hole injecting and transporting layer because itexcels in hole injecting and transporting ability.

Described below is the preferred embodiment wherein the inventivecompound is used in a hole injecting and transporting layer. The holeinjecting and transporting layer may be formed by evaporating theinventive compound or by dispersing the inventive compound in a resinbinder and coating the dispersion. Especially by evaporation, asatisfactory amorphous film is deposited.

Any of various organic compound used in conventional organic ELelements, for example, the organic compounds described in JP-A295695/1988, 191694/1990, and 000792/1991 may be concomitantly used inthe hole injecting and transporting layer. For example, any of aromatictertiary amines other than the inventive compounds, hydrazonederivatives, carbazole derivatives, triazole derivatives, imidazolederivatives, oxadiazole derivatives having an amino group, andpolythiophenes may be used in a layered or mixed manner along with theinventive compound.

Where the hole injecting and transporting layer is formed as comprisinga hole injecting layer and a hole transporting layer, two or morecompounds are selected in a proper combination from the compoundscommonly used in hole injecting and transporting layers, in this regard,it is preferred to laminate layers such that a layer of a compoundhaving a lower ionization potential may, be disposed adjacent to theanode (ITO etc.). It is also preferred to use a compound having betterthin film forming ability at the anode surface. This order of laminationalso applies where a plurality of hole infecting and transporting layersare provided. Such an order of lamination is effective for loweringdrive voltage and preventing current leakage and development and growthof local dark spots. Since evaporation is utilizable in manufacturingelements, thin films of about 1 to 10 nm thick can be formed uniform andpinhole-free. This restrains any change in color tone of light emissionand a drop of efficiency by re-absorption even if a compound having alow ionization potential and absorption in the visible range is used inthe hole injecting and transporting layer.

Polythiophene is a preferred organic compound to be combined wig thehole injecting and transporting layer containing the inventive compoundas a major component. From the standpoint of ionization potential, it isrecommended to deposit by evaporation polythiophene on an anode as ahole injecting layer or a first hole injecting and transporting layer ofgood thin film quality and then deposit the inventive compound theretoas a hole transporting layer or a second hole injecting and transportinglayer.

The polythiophees which can be used in the invention include a polymer Ahaving a structural unit of formula (28), a copolymer B havingstructural units of formulae (28) and (29), and a polymer C having astructural unit of formula (30). ##STR1060##

First thiophene polymer A is described. Polymer A has a structural unitof formula (28). For example, polymer A is represented by the followingformula (31). ##STR1061##

In formulae (28) and (31), each of R₃₁ and R₃₂ is a hydrogen atom, anaromatic hydrocarbon group or an aliphatic hydrocarbon group while R₃₁and R₃₂ may be identical or different. The aromatic hydrocarbon groupsrepresented by R₃₁ and R₃₂ may be substituted or substituted ones andpreferably have 6 to 15 carbon atoms. Exemplary substituents, if any,are alkyl, alkoxy, amino and cyano groups. Exemplary aromatichydrocarbon groups include phenyl, tolyl, methoxyphenyl, biphenyl andnaphthyl groups. The aliphatic hydrocarbon groups represented by R₃₁ andR₃₂ include alkyl and cycloalkyl groups which may be substituted orunsubstituted ones. Preferred are those groups having 1 to 6 carbonatoms, for example, methyl, ethyl, i-propyl and t-butyl groups.Preferably R₃₁ and R₃₂ are hydrogen atoms or aromatic hydrocarbongroups, with hydrogen being most preferred.

Polymer A in the layer has an average degree of polymerization,represented by m in formula (31), of 4 to 100, preferably 5 to 40, morepreferably 5 to 20. Polymer A may be either a homopolymer consisting ofidentical recurring units of formula (28) or a copolymer consistingessentially of recurring units of formula (28) having differentcombinations of R₃₁ and R₃₂. The copolymer may be any of random,alternate and block copolymers. Polymer A in the layer preferably has aweight average molecular weight of about 300 to about 10,000.

Polymer A is terminated with terminal groups, represented by X₁ and X₂in formula (31), which are hydrogen atoms or halogen atoms such aschlorine, bromine and iodine. The terminal groups introduced generallydepend on the starting material from which polymer A is synthesized.Alternatively, a suitable substituent may be introduced at the finalstage of polymerization reaction.

Preferably polymer A consists of structural units of formula (28)although it may contain less than 10 mol % of another monomericcomponent.

Some illustrative, preferred examples of polymer A are shown below bypicking up the combination of R₃₁ and R₃₂ in formula (28) or (31).

                  TABLE 13                                                        ______________________________________                                        Polymer A                                                                     Polymer    R.sub.31 R.sub.32                                                  ______________________________________                                        A-1        H        H          homopolymer                                    A-2        H        Ph         homopolymer                                    A-3        Ph       H          homopolymer                                    A-4        Ph       Ph         homopolymer                                    A-5        H        CH.sub.3   homopolymer                                    A-6        H        t-C.sub.4 H.sub.9                                                                        homopolymer                                    ______________________________________                                    

Next thiophene copolymer B is described copolymer B has structural unitsof formula (28) and (29). For example, copolymer B is represented by thefollowing formula (32). ##STR1062##

Formula (28) is as defined above. Then in formula (32), R₃₁ and R₃₂ areas defined above for formula (28).

In formulae (29) and (32), each of R₃₃ and R₃₄ is a hydrogen atom, anaromatic hydrocarbon group or an aliphatic hydrocarbon group while R₃₃and R₃₄ may be identical or different. Examples of the aromatic andaliphatic hydrocarbon groups represented by R₃₃ ad R₃₄ are the same asenumerated for R₃₁ and R₃₂, with their preferred examples being also thesame. Further R₃₃ and R₃₄ to together may form a ring which is fused tothe thiophene ring. A benzene ring is a typical fused ring.

Like polymer A, copolymer B in the layer has an average degree ofpolymerization, represented by v +w in formula (32), of 4 to 100,preferably 5 to 40, more preferably 5 to 20. The molar ratio of thestructural unit of formula (28) to the structural unit of formula (29)may range from about 10/1 to about 1/10. Copolymer 3 in the layer,preferably has a weight average molecular weight of about 300 to about10,000.

Copolymer B is terminated with terminal groups, represented by X₁ and X₂in formula (32), which are hydrogen atoms or halogen atoms as in polymerA. The terminal groups generally depend on the starting materials fromwhich copolymer B is synthesized.

Preferably copolymer B consists of structural units of formulae (28) and(29) although it may contain less than 10 mol % of another monomericcomponent. Copolymer B may be any of random, alternate and blockcopolymers, which are all encompassed by the structural formula (32).The structural units of each of formulae (28) and (29) may be identicalor different.

Some illustrative, preferred examples of copolymer B an shown below bypicking up the combination of R₃₁, R₃₂, R₃₃ and R₃₄ in formula (32).

                  TABLE 14                                                        ______________________________________                                        Copolymer B                                                                   Copolymer    R.sub.31 R.sub.32 R.sub.33                                                                             R.sub.34                                ______________________________________                                        B-1          H        H        H      H                                       B-2          H        CH.sub.3 H      H                                       B-3          H        Ph       H      H                                       B-4          H        Ph       Ph     Ph                                      ______________________________________                                    

Next thiophene polymer C is described. Polymer C is represented byformula (30) wherein R₃₃ and R₃₄ are as defined for formula (29), withtheir preferred examples being also the same.

X₁ and X₂ represent terminal groups and may be either identical ordifferent. Like the terminal groups of polymer A and copolymer B, theterminal groups represented by X₁ and X₂ are hydrogen atoms or halogenatoms such as chlorine, bromine and iodine. The terminal groups X₁ andX₂ generally depend on the starting material from which polymer C issynthesized.

Like polymer A and copolymer B, polymer C in the layer has an averagedegree of polymerization, represented by n in formula (30), of 4 to 100,preferably 5 to 40, more preferably 5 to 20. Polymer C may be either ahomopolymer consisting of recurring units having an identicalcombination of R₃₃ and R₃₄ or a copolymer consisting essentially ofrecurring units having different combinations of R₃₃ and R₃₄. Thecopolymer may be any of random, alternate and block copolymers. PolymerC in the layer preferably has a weight average molecular weight of about300 to about 10,000.

Preferably polymer C is of the structure shown by formula (30) althoughit may contain less than 10 mol % of another monomeric component likepolymer A and copolymer B.

Some illustrative, preferred examples of polymer C are shown below bypicking up the combination of R₃₃ and R₃₄ in formula (30).

                  TABLE 15                                                        ______________________________________                                        Polymer C                                                                     Copolymer  R.sub.33 R.sub.34                                                  ______________________________________                                        C-1        H        H            homopolymer                                  C-2        H        Ph           homopolymer                                  C-3        Ph       Ph           homopolymer                                  C-4        H        4-methoxyphenyl                                                                            homopolymer                                  C-5        CH.sub.3 CH.sub.3     homopolymer                                  C-6        H        CH.sub.3     homopolymer                                  ______________________________________                                    

In the practice of the invention, use of a polythiophene in the form ofpolymer C is most preferred. Polythiophenes may be used alone or inadmixture of two or more.

The polythiophenes used herein have a melting point of higher than 300°C. and some have no melting point. They can be evaporated and depositedin vacuum to form amorphous or microcrystalline thin films of quality.

In the above-mentioned embodiment: wherein the inventive compound isused in the hole injecting and transporting layer, the light emittinglayer contains a fluorescent or luminescent material which is a compoundhaving a light emitting function. The fluorescent or luminescentmaterial may be selected from compounds as disclosed in JP-A264692/1988, for example, quinacridone, rubrene, and styryl dyes aloneor in admixture. Other useful examples include metal complex dyes suchas tris(8-quinolinolato)aluminum, tetraphenylbutadiene, anthracene,perylene, coronene, and 12-phthaloperinone derivatives. By evaporatingthe organic fluorescent or luminescent material or by dispersing it in aresin binder and coating the dispersion, a light emitting layer isformed to a predetermined thickness.

For the electron injecting and transporting layer, there may be usedorganic metal complex derivatives such as tris(8-quinolinolato)aluminum,oxadiazole derivatives, perylene quinoline derivatives, quinoxalinederivatives, diphenylquinone derivatives, and nitro-substituted fluorenederivatives. In an embodiment wherein the electron injecting andtransporting layer also serves as a light emitting layer, use oftris(8-quinolinolato)aluminum is preferred. Like the hole injecting andtransporting layer and light emitting layer, the electron injecting andtransporting layer may be formed by evaporation.

Where the electron injecting and transporting layer is fodred ascomprising an electron injecting layer and an electron transportinglayer, two or more compounds are selected in a proper combination fromthe compounds commonly used in electron injecting and transportinglayers. In this regard, it is preferred to laminate layers such that alayer of a compound having a greater electron affinity may be disposedadjacent to the cathode. This order of lamination also applies where aplurality of electron injecting and transporting layers are provided.

The organic compound layer may further contain a single oxygen quencher.Exemplary quechers include rubrene, nickel complexes,diphenylisobenzofuran, and tertiary amines, with the rubrene beingpreferred. When combined with the inventive compound, the quencher maybe present in an amount of less than 10 mol % of the inventive compound.

In okn preferred embodiment of the present invention, the organic coldlayer or layers are preferably doped with rubrene. Doping may be carriedout throughout the organic compound layer, preferably throughout thehole injecting and transporting layer. It is believed preferable thatrubrene be present in a carrier recobination region, a light emittingregion and the proximity thereof, for example, the interface of anorganic compound layer in contact with a hole injecting and transportinglayer. Then doping need not necessarily be carried out throughout thehole injecting and transporting layer. Therefore doping may be limitedto a half area of the hole injecting and transporting layer which isdisposed adjacent to the light emitting layer (which may also serve asan electron injecting and transporting layer) or the electron injectingand transporting layer (where the hole injecting and transporting layeralso serves as a light emitting layer) although doping is generallycarried out throughout the hole injecting and transporting layer. Insome cases, doping may be carried out throughout the hole injecting andtransporting layer or a half area of the hole injecting a transportinglayer which is disposed adjacent to the light emitting layer or theelectron injecting and transporting layer and a half region of the lightemitting layer or electron injecting and transporting layer which isdisposed adjacent to the hole injecting and transporting layer. Combineduse of the inventive compound and rubrene is preferred particularly inthe hole injecting and transporting layer.

The doping concentration of rubrene is preferably about 0.1 to 500 byweight, more preferably about 0,1 to 30% by weight, most preferablyabout 0.1 to 20%; by weight of the entire layer to be doped becausehigher concentrations of rubrene can cause concentration quenching.

Besides rubrene, it is alo contemplated to dope with other fluorescentor luminescent materials.

In one preferred embodiment of the invention, interposed between a layercontaining the inventive compound and a layer contains a compound havinganother function is a mix layer containing a mixture of both thecompounds, especially as a light emitting layer. For enhancing luminousintensity, the mix layer may be doped with a compound having a lightemitting function (or fluorescent or luminescent material).

Since the inventive compound has a hole injecting Me transportingfunction, it is especially preferred to provide a mix layer containing amixture of the inventive compound and a compound having an electroninjecting and transporting function (inclusive of a compound furtherhaving a light emitting function) as a light emitting layer. Thecompound having an electron injecting and transporting function used inthis mixture may be selected from the previously mentioned compounds forelectron injection and transportation. Specifically use oftris(8-quinolinolato)aluninum is preferred.

In the mix layer, the compounds having a hole or electron injecting andtransporting function may be used alone or in admixture of two or more.The compound having a hole injecting and transporting function used inthis mixture may be selected from the previously mentioned compounds forhole injecting and transporting as well as the inventive compounds.

In one especially preferred structure, a hole injecting and transportinglayer containing the inventive compound is disposed on a hole injectingand transporting layer containing polythiopheze, and a mix layercontaining a mixture of the inventive compound and a compound having anelectron injecting and transporting function is interleaved between thehole and electron injecting and transporting layers as a light emittinglayer.

With respect to the mix ratio, which depends on carrier mobility, it ispreferred that the inventive compound occupies about 30 to 70%, morepreferably about 40 to 60%, especially about 50% by weight of the mixlayer. Differently stated, the weight ratio of the inventive compound tothe compound having an electron injecting and transporting functionpreferably ranges from about 30/70 to 70/30, more preferably from about40/60 to 60/40, especially about 50/50.

The thickess of the mix layer preferably ranges from the thicknesscorresponding to a single molecule layer to less than the thickness ofan organic compound layer. More particularly the mix layer has athickness of from about 1 to about 85 nm, =ere preferably about 5 to 60nm, most preferably about 5 to 50 nm.

Preferably the mix layer is formed by co-deposition, that is, bysimultaneously evaporating the compounds from distinct sources. If boththe compounds have equal or close vapor pressure or evaporationtemperature, they may be pre-mixed in a common evaporation boat, fromwhich they are evaporated together. In the mix layer, preferably boththe compounds are uniformly mixed although the compounds can be presentin island form.

It is to be noted that the mix layer may also be used as an organiccompound layer other than the light emitting layer. However, it ispreferred that the mix layer for part of organic compound layersincluded in the element. If all the organic compound layers are mixlayers, the element sometimes fails to provide uniform light emission athigh luminance.

In the preferred embodiment, the inventive compound is used in the holeinjecting and transporting layer as mentioned above. The difference inionization potential Ip between the hole injecting and transportinglayer and a light emitting layer disposed adjacent thereto (which mayalso serve as electron injecting and transporting layer) shouldpreferably be at least 0.25 eV, especially 0.25 to 0.40 eV. It isunderstood that where a layer containing the inventive compound is alayer having a hole injecting and transporting function and also servingas a light emitting layer, the layer disposed adjacent thereto is aelectron injecting and transporting layer, and accordingly thedifference in ionization potential Ip in this case is that between thelayer containing the inventive compound and the electron injecting andtransporting layer. Note that the inventive compounds have an ionizationpotential Ip of about 5.0 to 5.4 eV in absolute value.

It is to be noted that the ionization potential Ip is determined byevaporating a compound onto a glass substrate having an ITO transparentelectrode or slide glass to form a compound mono-layer film of about 10to 200 nm thick and measuring the ionization potential of the samplefilm by means of a low energy electron spectrometer Surface Analyzermodel AC-1 manufactured by Riken Kiki Co., Ltd. according to Shirahashi,Isobe & uda, Electronic Parts and Materials, 123 (1985).

FIG. 2 shows the construction of the low energy electron spectrometersystem. The spectrometer generally designated at 10 includes aultraviolet lamp 11, a monochrometer 12, a detector 13, a low energyelectron counter 14, a controller 15, a computing/display unit 16, andan X-Y stage 17. On measurement, a sample S rests on the X-Y stage 17.

The UV lamp 11 in the form of a deuterium discharge lamp emits UVradiation toward the monochrometer 12 through which a light beam havinga wavelength of 200 to 360 nm is passed and directed to the surface ofthe sample S. The light beam having a wavelength of 200 to 360 nm hasenergy of 6.2 to 3.4 eV as converted according to the equation:E=hv=h(c/λ) wherein E is an energy, h is Planck's constant, v is afrequency, and λ is a wavelength, When the light is swept from a lowerexcitation energy level to a higher excitation energy level, electronemission due to the photoelectric effect starts at a certain energylevel. This energy level is generally known as a photoelectric workfunction. The thus emitted photoelectrons are detected and counted bythe detector 13 and the low energy electron counter 14. The count issubject to arithmetic operations including a background correction and acorrection for a count loss during a dead time and then displayed on thedisplay unit 16 for indicating an electron emission as a function ofexcitation energy (basic characteristic) as shown in FIG. 3. As seenfrom the basic characteristic, the relationship between thephotoelectron yield (count per second, cps) and the excitation energy(eV) is linear provided that a factorial of photoelectron yield(cps)^(n) is on the ordinate and the excitation energy is an theabscissa. The value of n is generally 1/2. The controller 15 serves forwavelength driving of the monochrometer 12, control of the sampleposition on the X-Y stage 17, and count control of the low energyelectron counter 14.

Therefore, the photoelectron work function obtained from FIG. 3 is theionization potential Ip used herein.

Where a layer containing the inventive compound further contains anothercompound, the ionization potential Ip of this layer is regarded equal tothe ionization potential Ip measured from a single layer film of theinventive compound if the inventive compound is a major component(typically having a content of more than 50% by weight). Where a layerto be compared with the inventive compound-containing layer contains twoor more compounds, the ionization potential Ip of this layer is regardedequal to the ionization potential Ip measured from a single layer filmof the primary compound constituting the majority (typically having acontent of more than 50% by weight).

As a general rule, the absolute value of ionization potential Ip of asingle layer film of the inventive compound is lower than that of acompound to be compared therewith.

It should be understood that the concept of ionization potential is notapplicable to the arrangement wherein a mix layer is interposed betweenthe relevant layers.

In the practice of the invention, the cathode is preferably made of amaterial having a low work function, for example, Li, Na, ZV, Al, Ag, Inand alloys containing at least one of those metals. The cathode shouldpreferably be microcrystalline, especially amorphous. The cathode ispreferably about 10 to 1,000 nm thick.

In order that the EL element produce plane light emission, at least oneof the electrodes should be transparent or semi-transparent. Since thematerial of the cathode is limited as mentioned just above, it ispreferred to select the material and thickness of the anode so as toprovide a transmittance of at least 80% to Me emitted radiation. Forexample, the anode is preferably made of indium tin oxide (ITO), SnO₂,Ni, Au, Pt, Pd, and doped polypyrrole. The anode preferably has athickness of about 10 to 500 nm. In order that the element be morereliable, the drive voltage should be low. For example, ITO having 10 to30 Ω/cm² is preferred.

The substrate may be made of any desired material although a transparentor semi-transparent material such as glass and resins is used in theillustrated embodiment wherein light exits from the substrate side. Thesubstrate may be provided with a color or fluorescent filter film, acolor-conversion film or layer or dielectric reflecting film forcontrolling emission light color. Where the substrate is made of anopaque material, the layer stacking order may be reversed from thatshown in FIG. 1.

Next, it is described how to prepare the organic EL element using theinventive compound. The cathode and anode are preferably formed by gasphase deposition techniques such as vacuum evaporation and sputtering.The light emitting layer and hole and electron injecting andtransporting layers are preferably formed by vacuum evaporation becausehomogeneous thin films are available. By utilizing vacuum evaporation,there is obtained a homogeneous thin film which is amorphous or has agrain size of less than 0.1 μm. The lower limit of grain size isgenerally about 0.001 μm. If the grain size is more than 0.1 μm, unevenlight emission takes place and the drive voltage of the element must beincreased with a substantial lowering of electric charge injectionefficiency.

The conditions for vacuum evaporation are not critical although a vacuumof 10⁻³ Pa or lower and an evaporation rate of about 0.1 to 1 nm/sec.are preferred. It is preferred to successively form layers in vacuumbecause the successive formation in vacuum can avoid adsorption ofimpurities at the interface between the layers, thus ensuring highquality and a lower drive voltage.

In th embodiment wherein the respective layers are formed by vacuumevaporation, where it is desired for a single layer to contain two ormore compounds, boats having the compounds received therein areindividually temperature controlled to achieve co-deposition. It is alsoacceptable to evaporate a pre-mix of two or more compounds. Alsoemployable are solution coating techniques such as spin coating, dippingand casting and Langmuir-Blodgett'S technique. For the solution coating,the inventive compound may be dispersed in a matrix material such as apolymer.

The organic EL element of the invention is generally of the DC drivetype while it can be of the AC or pulse drive type. The applied voltageis generally about 2 to 20 volts.

It is understood that the inventive compounds are also applicable asorganic semiconductor materials having donor property to photo-electrictransducer elements other than the organic EL element, for example,photo-cells and photo-sensors. They are also useful as thermochromicmaterials utilizing transition between amorphous and crystalline states.

EXAMPLE

Examples of the present invention are given below by way of illustrationand not by way of limitation. Herein "mp" is a melting point and "Tg" isa glass transition temperature.

Example 1

Synthesis of N,N,N',N'-tetra(3-biphenylyl)benzidine, compound No. I-1

A 2-1atmospheric hydrogenation reactor was charged with 250 g (1.26 mol)of m-nitrobiphenyl, 12.5 q of 5% Pd-Cl, and 1250 ml of ethanol. Atheoretical amount of hydrogen gas was absorbed at room temperature. Thecatalyst was removed by filtration and the filtrate was distilled of thesolvent, obtaining 212 g of m-aminobiphenyl (yield 99.9%). Another batchof reaction was effected on the same scale except that 254 g (1.28 mol)of m-nitrobiphenyl was used, obtaining 215 g of m-aminobiphenyl (yield99.7%),

A 10-1 reactor was charged with 775 m. of conc, hydrochloric acid, 775ml of water, and 775 g of ice, and 125 g (0.740 mol) of m-aminobiphenylwas sided therein. To the reactor maintained below 0° C., 750 ml of anaqueous solution of 56.3 g (0.816 mol) sodium nitrite was added dropwiseover 30 minutes and stirring was continued for a further 50 minutes atthe temperature. To the resulting diazonium salt aqueous solutionmaintained below 0° C., 1250 ml of an aqueous solution of 185 g (1.12mol) potassium iodide was added dropwise over one hour. After addition,stirring was continued for one hour at the temperature and then for 2hours at room temperature.

The reaction solution was extracted with ethyl acetate. The organiclayer was washed with water, dried over magnesium sulfate, and distilledof the solvent, obtaining a crude crystal. Another batch of reaction waseffected on the same scale. The resulting crude crystals were combinedtogether and purified through a silica gel column with n-hexane,obtaining 297 g of m-iodobiphenyl (yield 71.7% for the two batchescombined).

A 2-1 reactor was charged with 140 g (0.828 mol) of maminobiphenyl, 232g (0.829 mol) of m-iodobipheyl, 63.1 g (0.457 mol) of potassiumcarbonate, 13.9 g of copper powder, and 800 ml of nitrobenzene. In anargon stream, the contents were heated under reflux for 32 hours. At theend of reaction, the insoluble was removed by filtration and thefiltrate was distilled of the solvent. The still residue was purifiedthrough a silica gel column with a 4/1 mixture of n-hexane and toluene,obtaining 44.5 g of di(3-biphenyl)amine of high purity (yield 16.7%).

A 500-ml reactor was charged with 44.5 g (0.139 mol) ofdi(3-biphenyl)amine, 27.6 g (0.0680 mol) of 4,4'-diiodobiphenyl, 34.3 g(0.249 mol) of potassium carbonate, 2.3 g of copper powder, and 180 mlof nitrobenzene. In an argon stream, the contents were heated underreflux for 24 hours. At the end of reaction, the insoluble was removedby filtration and the filtrate was distilled of the solvent. The stillresidue was purified through a silica gel column with a 3/1 mixture ofn-hexane and toluene, obtaining 30 g ofN,N,N',N'-tetra(3-biphenylyl)benzidine of primary purity grade (yield55.7%). It was further purified by recrystallization from toluene,obtaining 6.0 g of a 99.58% pure fraction and 5.0 g of a 99.23% purefraction (combined yield 20.496). Further purification by sublimationyielded 8.0 g of a 99.99% pure product.

mass analysis; m/e 792 (M⁺).

IR absorption spectrum FIG. 4.

NM spectrum; FIG. 5.

Differential scanning calorimetry (DSC): mp 207.4° C. Tg 95. 8° C.

Example 2

Synthesis of N,N,N',N'-tetra(4-biphenyl)berizidine, compound No. II-1

A reactor was charged with 72.5 g (0.429 mol) of 4-aminobiphenyl, 120 g(0,429 mol) of 4-iodobiphonyl, 32.6 g (0.236 mol) of potassiumcarbonate, 6.8 g (0.107 mol) of copper, and 430 ml of nitrobezene.Reaction was effected overnight at 210° C. At the end of reaction, thereaction solution was allowed to cool down, the copper salts wereremoved by vacuum filtration, and the filtrate was washed withchloroform and vacuum distilled of the solvent. To the residue was added500 ml of methanol. On cooling, crystals precipitated and were recoveredby filtration. The thus recovered crystals, 49 g, was dissolved in 250ml of dimnethylfoxmamide (DMF) with heating. The solution was cooledwith water for allowing tribiphenylamine by-product to precipitate,which was removed by filtration. The filtrate was poured into 1000 ml ofwater for allowing crystals to precipitate. The precipitate wasrecovered by filtration and washed with water and t with methanol.

The thus obtained wet crystals, 35 g, were recrystallized from 750 ml oftoluene, obtaining di(4-biphenyl)amine in yellowish green flake crystalform. The mother liquor was concentrated to recover secondary crystals.The combined amount was 19 g (yield 13.8%).

A reactor was charged with 15 g (0.0467 mol) of di(4-biphenyl)amine, 9.5g (0,0234 mol) of 4,4'-diiodobiphenyl, 9.7 g (0.0702 mol) of potassiumcarbonate, 0.74 g (0.0117 mol) of copper, and 76 ml of nitrobenzens.Reaction was effected for two days at 220° C. At the end of reaction,750 ml of DMF was added to the reaction solution, from which the coppersalts were removed by filtration while hot. The filtrate was cooled downand the precipitating crystals were recovered by filtration. The thusobtained wet crystals, 25 g, were recrystallized three times from a100-fold volume of toluene, obtaining 9 g of the end product,N,N,N',N'-tetra(4-biphenylyl)benzidine in pale yellow crystal form(yield 48.6%). Further purification by sublimation yielded a 99.99% pureproduct.

mass analysis: m/e 792 (M⁺).

IR absorption spectrum: FIG. 6.

NMR spectrum: FIG. 7.

DSC: mp 267.7° C. Tg 131.8° C.

Example 3

Synthesis of N,N'-diphezyl-N,N'-di(3-biphenylyl) benzidine, compound No.VII-1

A 10-1 reactor was charged with 155 ml of conc. hydrochloric acid, 155ml of water, and 155 g of ice, and 25 g (0.148 mol) of m-aminobiphenylwas suspended therein. To the reactor maintained below 0° C., 150 ml ofan aqueous solution of 11.3 g (0.164 mol) sodium nitrite was addeddropwise over 30 minutes and stirring was continued for a further 50minutes at the temperature. To the resulting diazonium salt aqueoussolution maintained below 0° C., 250 ml of an aqueous solution of 37 g(0.223 mol) potassium iodide was added dropwise over one hour. Afteraddition, stirring was continued for one hour at the temperature andthen for 2 hours at room temperature.

The reaction solution was extracted with ethyl acetate. The organiclayer was washed with water, dried over magnesium sulfate, and distilledof the solvent, obtaining a crude crystal. The crude crystal waspurified through a silica gel column with n-hexane, obtaining 28 g ofm-iodobiphenyl.

300-ml reactor was charged with 10 q (0.0298 mol) ofN,N'-diphenylbenzidie, 25 g (0.0893 mol) of m-iodobiphenyl, 12.3 g(0.0891 mol) of potassium carbonate, 2.6 g of copper powder, and 150 mlof nitrobenzene. In an argon stream, the contents were heated underreflux for 24 hours. At the end of reaction, the insoluble was removedby filtration and the solvent was distilled off from the filtrate. Thestill residue was purified through a silica gel column with a 5/1mixture of n-hexane and ethyl acetate, obtaining 15 g ofN,N'-diphenyl-N,N'-di(3-biphenylyl)benzidine of primary purity grade(yield 78.89%. It was further purified by recrystallization from tolueneand train sublimation, obtaining 10.6 g of a 99.9% pure product (yield55.6%). Further purification by sublimation yielded a 99,99% pureproduct.

mass analysis: m/e 640 (M⁺).

IR absorption spectrum: FIG. 8.

NMR spectrum: FIG. 9.

DSC: mp 189.8° C. Tg 83.6° C.

Example 4

Synthesis of N,N'-diphenyl-N,N'-bis4'-(N-phenyl-N-3-methylphenylamino)biphenyl-4-yl!benzidine, compound No.X-10

A 500-ml reactor was charged with 33.6 g (0.10 mol) ofN,N'-diphenylbenzidine, 25.0 g (0.11 mol) of m-iodotoluene, 27.6 g (0.2mol) of potassium carbonate, 2.6 g of copper powder, and 200 ml ofnitrobenzene. In an argon stream, the contents were heated under refluxfor 24 hours. At the end of reaction, the insoluble was removed byfiltration and the solvent was distilled off from the filtrate. Thestill residue was purified twice through a silica gel column with a1/2mixture of n-hexane and toluene, obtaining 28.10 g ofN,N'-diphenyl-N-4-(N-phenyl-N-3-methylphenylamino)-biphenyl-4-yl!benzidine (yield 42%).

A 500-ml reactor was charged with 8.1 g (0.02 mol) of4,4'-diiodobiphenyl, 28.1 g (0.02 mol) of N,N'-diphenyl-N-4(N-phenyl-N-3-methylphenylamino)-biphenyl-4-yl!benzidine, 11.04 g (0.08mol) of potassium carbonate, 1.0 g of copper powder, and 100 ml ofnitrobenzene. In an argon stream, the contents were heated under refluxfor 24 hours. At the end of reaction, the insoluble was removed byfiltration and the solvent was distilled off from the filtrate. Thestill residue was purified twice through a silica gel column with a 2/1mixture of n-he and toluene, obtaining 11.62 g of highly pureN,N'-diphenyl-N,N'-bis4'-(N-phenyl-N-3-methylphoylamino)-biphenyl-4-yl!benzidine (yield 58%).It was further purified by recrystallization from a solvent mixture ofhexane and toluene, obtaining 7.3 g of a 99.9% pure, pale yellow, clear,amorphous mass.

mass analysis: m/e 1002 (M⁺).

IR absorption spectrum: FIG. 10.

NMR spectrum: FIG. 11.

DSC: mp not observed (amorphous from the initial)Tg 132° C.

Example 5

Synthesis of N,N'-diphenyl-N,N'-bis4'-(N,N-di-3-biphenylylamino)biphenyl-4-yl!benzidine, compound No. X-3

A 300-ml reactor was charged with 16.1 g (0.050 ml) ofdi(3-biphenylyl)amino, 20.3 g (0.050 mol) of 4,4'-diiodobiphenyl, 13.8 g(0.10 mol) of potassium carbonate, 1.0 g of copper powder, and 100 ml ofnitrobenzene. In an argon stream, the contents were heated under refluxfor 24 hours. At the end of reaction, the insoluble was removed byfiltration and the solvent was distilled off from the filtrate. Thestill residue was purified through a silica gel column with a 5/1mixture of n-hexane and toluene, obtaining 12.0 g of 4'-N,N'-di(3-biphenylylamio)!-4-iodo-1,1'-biphenyl (yield 40%).

A 300-ml reactor was charged with 12.0 g (0.020 mol) of 4'- N,N'-di(3-biphenylylamino)-!4-iodo-1,1'-biphenyl, 3.03 g (0.009 mol) ofN,N'-diphenylbenzidine, 5.52 g (0.04 mol) of potassium carbonate, 0.5 gof copper powder, and 100 ml of nitrobenzene. In an argon stream, thecontents were heated under reflux for 24 hours. At the end of reaction,the insoluble was removed by filtration and the solvent was distilledoff from the filtrate. The still residue was purified twice through asilica gel column with a 2/1 mixture of toluene and n-hexane, obtaining6.90 g of N,N'-diphenyl-N, N'-bis 4'-(N,N-di-3-biphenylylamino)biphenyl-4-yl!benzidine (yield 60%). It was further purified byrecrystallization from toluene, obtaining 5.2 g of a 99.9% pure, paleyellow, clear, amorphous mass.

This compound was also identified by mass analysis, IR, and NMR as inExample 4.

The remainder of the previously exemplified compounds were synthesizedby the same procedures as above and identified by mass analysis, IR andNMR.

Example 6

A glass substrate having an ITO transparent electrode (anode) of 200 nmthick was subjected to ultrasonic cleaning with neutral detergent,acetone, and ethanol. The substrate was pulled up from boiling ethanol,dried, and further subjected to UV/ozone cleaning. The substrate wassecured by a holder in an evaporation chamber, which was evacuated to avacuum of 1×10⁻⁴ Pa or lower.

Then the compound (I-1) of Example 1 was evaporated at a deposition rateof 0.2 nm/sec. to deposit a transparent amorphous thin film of 55 nmthick. It was allowed to stand in a constant temperature chamber at 30°C./RH 100% and 60° C./RH 90%, both severer than the atmospheric air,over 10 months. The thin film underwent no crystallization andmaintained a stable amorphous state, indicating good thin film-formingability and storage stability. A similarly deposited film was found tohave ionization potential Ip of 5.35 eV as measured by a low energyelectron spectrometer Model AC-1 manufactured by Riken Keiki Co., Ltd.

Example 7

Using compounds (II-1) and (VII-1) of Examples 2 and 3, experiments weredone as in Example 6. Similarly no crystallization occurred duringstorage over 10 monthly The evaporated films had an ionization potentialIp of 5.36 eV and 5.38 eV.

Example 8

Using compounds (X-10) and (X-3) of Examples 4 and 5, experiments weredone as in Example 6. Similarly no crystallization occurred duringstorage over 10 months. The evaporated films had an ionization potentialIp of 5.32 eV and 5.28 eV.

Comparative Example 1

Thin films were deposited as in Example 6 except that the compound ofExample 1 was replaced by compound (1): N,N'-diphelyl-N,N'-di(3-methylphenyl)-4,4'-diamino-1,1'-biphenyl (mp: 171.2° C., Tg: 61.3°C.) or compound (2): 1,1'-bis(4-di-p-tolylaminophenyl) cyclohexane (mp:187.8° C., Tg: 79.9° C.). The thin films were allowed to stand in aconstant temperature chamber at 30° C./RH 100%. Although the films wereallowed to stand in a milder temperature environment than Examples 6 to8, crystallization started on the third day in the film of compound (1)and on the 30th day in the film of compound (2).

As in Example 6, the film of compounds (1) and (2) were measured forionization potential. Both had an Ip of 5.40 eV.

Example 9

A glass substrate having an ITO transparent electrode (anode) of 200 nmthick was subjected to ultrasonic cleaning with neutral detergent,acetone, and ethanol. The substrate was pulled up from boiling ethanol,dried, and further subjected to UV/ozone cleaning. The substrate wassecured by a holder in an evaporation chamber, which was evacuated to avacuum of 1×10⁻⁴ Pa or lower.

First compound (I-1) of Example 1 was evaporated at a deposition rate of0.2 nm/sec. to a thickness of 75 nm, forming a hole injecting andtransporting layer.

With the vacuum kept, tris(8-quinolinolato)aluminum was evaporated at adeposition rate of 0.2 nm/sec. to a thickness of 50 n forming anelectron injecting and transporting/light emitting layer.

With the vacuum kept further, MgAg (weight ratio 10:1) was evaporated ata deposition rate of 0.2 nm/sec. to a thickness of 200 nm to form acathode, obtaining an organic EL element.

With a DC voltage applied, the EL element was continuously driven at aconstant current density of 10 mA/cm² in-a dry atmosphere. At theinitial, mission of yellowish green light (maximum wavelength λmax=500nm) at a luminance of 400 cd/m² was observed with a drive voltage of 6.5V. A half life of luminance was 600 hours, during which the drivevoltage increased 4.0 V. The deposited film oftris(8-quinolinolato)aluminum serving as the light emitting layer had anIp of 5.64 eV, with the difference in Ip from the film of compound (I-1)serving as the hole injecting and transporting layer being 0.29 eV.

Example 10 and 11

EL elements were manufactured as in Example 9 except that compound (I-1)was replaced by compounds (11-1) and (VII-1) of Examples 2 and 3. Theywere similarly tested.

Comparative Example 2 and 3

EL elements were manufactured as in Example 9 except that compound (I-1)was replaced by compounds (1) and (2) of Comparative Example 1. Theywere similarly tested.

The results of Examples 9-11 and Comparative Example 2-3 are show intable 16.

                  TABLE 16                                                        ______________________________________                                                                         Dif-                                                Initial     Luminance half-life                                                                         ferential                                    Com-     Luminance Voltage Time  Voltage Ip                                   pound    (cd/m.sup.2)                                                                            (V)     (hr.) Rise (V)                                                                              (eV)                                 ______________________________________                                        E9   (I-1)   400       6.5   600   4.0     0.29                               E10  (II-1)  420       6.5   620   4.1     0.28                               E11  (VII-1) 380       6.6   500   3.8     0.26                               CE2  (1)     300       5.2   120   7.6     0.24                               CE3  (2)     360       8.5    <19* breakdown                                                                             0.24                               ______________________________________                                         *The drive voltage rose to 11.5 V after 3 hours, and the element broke        down on the next day (after 19 hours).                                   

Examples 12 and 13

EL elements were manufactured as in Example 9 except that compound (I-1)was replaced by compounds (X-10) and (X-3) of Examples 4 and 5. Theywere similarly tested. The results were at least comparable to those ofExample 9. The differential Ip from tris(8-quinolinolato)aluminum was0.32 eV for compound (X-10) of Example 4 and 0.36 eV for compound (X-3)of Example 5.

Example 14

A glass substrate having an ITO transparent electrode (anode) of 200 nmthick was subjected to ultrasonic cleaning with neutral detergent,acetone, and ethanol. The substrate was pulled up from boiling ethanol,dried, and further subjected to UV/ozone cleaning. The substrate wassecured by a holder in an evaporation chamber, which was evacuated to avacuum of 1×10⁻⁴ Pa or lower.

First poly(thiophene-2,5-diyl) was evaporated at a deposition rate of0.1 nm/sec. to a thickness of 20 nm, forming a first hole injecting andtransporting layer.

Then with the vacuum kept, compound (I-1) of Example 1 was evaporated ata deposition rate of 0.2 nm/sec. to a thickness of 55 nm, forming asecond hole injecting and transporting layer.

With the vacuum kept, tris(8-quinolinolato)aluminum was evaporated at adeposition rate of 0.2 nm/sec. to a thickness of 50 nm, forming anelectron injecting and transporting/light emitting layer. With thevacuum kept further, MgAg (weight ratio 10:1) was evaporated at adeposition rate of 0.2 nm/sec. to a thickness of 200 nm to form acathode, obtaining an organic EL element.

With a DC voltage applied, the EL element was continuously driven at aconstant current density of 10 mA/cm² in a dry atmosphere. At theinitial, emission of yellowish green light (maximum wavelength λmax=500nm) at a luminance of 350 cd/m² was observed with a drive voltage of 6.0V. A half life of luminance was 1600 hours, during which the drivevoltage increased 2.3 V. No development or growth of dark spots wasobserved. Thereafter, no current leakage occurred and stable lightmission continued.

These results fully satisfy the requirements for the EL element to beapplied as a display. As an accelerated lifetime test, the EL elementwas continuously driven at a higher current density of 40 mA/cm²,finding a high luminance of 1400 cd/m² at the initial and a half life of400 hours, with a concomitant drive voltage rise of 5.0 V.

Examples 15 and 16

EL elements were manufactured as in Example 14 except that compound(I-1) was replaced by compounds (II-1) and (VII-1) of Examples 2 and 3.They were similarly tested at a current density of 10 mA/cm².

The results of the EL elements of Examples 14-16 at a current density of10 MA/cm² are shown in Table 17.

                  TABLE 17                                                        ______________________________________                                                                         Dif-                                                Initial     Luminance half-life                                                                         ferential                                    Com-     Luminance Voltage Time  Voltage Ip                                   pound    (cd/m.sup.2)                                                                            (V)     (hr.) Rise (V)                                                                              (eV)                                 ______________________________________                                        E14  (I-1)   350       6.0   1600  2.3     0.29                               E15  (II-1)  360       5.8   1800  2.5     0.28                               E16  (VII-1) 330       5.8   1500  2.3     0.26                               ______________________________________                                    

Example 17 and 18

EL elements were manufactured as in Example 14 except that compound(I-1) was replaced by compounds (X-10) and (X-3) of Examples 4 and 5.They were similarly tested at a current density of 10 mA/cm². Theresults were at least comparable to those of Example 14.

Example 19

A glass substrate having an ITO transparent electrode (anode) of 200 nmthick was subjected to ultrasonic clearing with neutral detergent,acetone, and ethanol. The substrate was pulled up from boiling ethanol,died, and further subjected to UV/ozone cleaning. The substrate wassecured by a holder in an evaporation chamber, which was evacuated to avacuum of 1×10⁻⁴ Pa or lower.

First compound (I-1) of Example 1 and rubrene were evaporated andco-deposited at a rate of 0.2 nm/sec. and 0.02 nm/sec. to a totalthickness of 75 nm, forming a hole injecting and transporting layer.

With the vacuum kept, tris(8-quinolinolato)aluminum was evaporated anddeposited at a rate of 0.2 nm/sec. to a thickness of 50 nm, forming anelectron injecting and transporting/light emitting layer.

With the vacuum kept further, NgAg (weight ratio 10:1) was evaporatedand deposited at a rate of 0.2 nm/sec. to a thickness of 200 nm to forma cathode, obtaining an organic EL element.

With a DC voltage applied, the EL element was continuously driven at aconstant current density of 10 mA/cm² in a dry atmosphere. At theinitial, emission of yellow light (maximum wavelength λmax=550 nm) at aluminance of 550 cd/m² was observed with a drive voltage of 6.2 V. Ahalf life of luminance was 1,500 hours, during which the drive voltageincreased 2.8 V.

Example 20 and 21

EL elements were manufactured as in File 19 except that compound (I-1)was replaced by compounds (II-1) and (VII-1) of Examples 2 and 3. Theywere similarly tested.

The results of the EL elements of Examples 12-14 are shown in Table 18.

                  TABLE 18                                                        ______________________________________                                                                         Dif-                                                Initial     Luminance half-life                                                                         ferential                                    Com-     Luminance Voltage Time  Voltage Ip                                   pound    (cd/m.sup.2)                                                                            (V)     (hr.) Rise (V)                                                                              (eV)                                 ______________________________________                                        E19  (I-1)   550       6.2   1500  2.8     0.29                               E20  (II-1)  580       6.1   1600  3.0     0.28                               E21  (VII-1) 530       6.2   1300  2.9     0.26                               ______________________________________                                    

Examples 22 and 23

EL elements were manufactured as in Example 19 except that compound(I-1) was replaced by compounds (X-10) and (X-3) of Examples 4 and 5.They were similarly tested. The results were at least comparable tothose of Example 19.

Example 24

A glass substrate having an ITO transparent electrode (anode) of 200 nmthick was subjected to ultrasonic cleaning with neutral detergent,acetone, and ethanol. The substrate was pulled up from boiling ethanol,dried, and further subjected to UV/ozone cleaning. The substrate wassecured by a holder in an evaporation chamber, which was evacuated to avacuum of 1×10⁻⁴ Pa or lower.

First poly(thiophene-2,5-diyl) was evaporated at a deposition rate ofabout 0.1 nm/sec. to a thickness of about 20 nm, forming a first holeinjecting and transporting layer.

Then the vacuum chamber was released to the atmospheric air andevacuated again to a vacuum of 1×10⁻⁴ Pa or lower. The compound (I-1) ofExample 1 and rubrene were evaporated and co-deposited at a rate of0.1-0.2 nm/sec. and 0.01-0.02 nm/sec. to a total thickness of about 55nm, forming a second hole injecting and, transporting layer.

With the vacuum kept, tris(8-quinolinolato)aluminum was evaporated anddeposited at a rate of 0.1-0.2 nm/sec. to a thickness of about 50 mm,forming an electron injecting and transporting/light emitting layer.

With the vacuum kept further, MgAg (weight ratio 10:1) was evaporated ata deposition rate of 0.2 nm/sec. to a thickness of about 200 nm to forma cathode, obtaining an organic EL element.

With a DC voltage applied, the EL element was continuously driven at aconstant current density of 10 mA/cm² in a dry atmosphere. At theinitial, emission of yellow light (maximum wavelength λmax=550 nm) at aluminance of 420 cd/m² was observed with a drive voltage of 6.2 V. Ahalf life of luminance was 2,000 hours, during which the drive voltageincreased 4.9 V.

These results fully satisfy the requirements for the EL element to beapplied as a display. As an accelerated lifetime test, he EL element wascontinuously driven at a higher current density of 40 mA/cm², finding ahigh luminance of 1490 cd/m² at the initial and a half Life of 500hours, with a concomitant drive voltage rise of 3,5 V.

Example 25

An EL element was manufactured as in Example 24 except that compound(X-10) of Example 4 was use in the second hole injecting andtransporting layer instead of compound (I-1). It was similarly tested.The results were at least comparable to those of Example 24.

Example 26

A glass substrate having ITO transparent electrode (anode) of 200 nmthick was subjected to ultrasonic cleaning with neutral detergent,acetone, and ethanol. The substrate was pulled up from boiling ethanol,dried, and further subjected to UV/ozone cleaning. The substrate wassecured by a holder in an evaporation chamber, which was evacuated to avacuum of 1×10⁻⁴ Pa or lower.

First compound (I-1) of Example 1 was evaporated at a deposition rate of0.1-0.2 nm/sec. to a thicknees of about 55 nm, forming a hole injectingand transporting layer.

Then with the vacuum kept, the hole injecting and transporting materialand tris(8-quinolinolato)aluminum as an electron injecting andtransporting material were evaporated and co-deposited at dsubstantially equal rate of 0.1-0.2 nm/sec. to form a mix layer of about40 nm thick as a light emitting layer.

With the vacuum kept, the electron injecting and transporting materialwas evaporated and deposited at a rate of 0.1-0.2 nm/sec. to a thicknessof about 30 nm, forming a electron injecting and transporting layer.

With the vacuum kept further, NgAg (weight ratio 10:1) was evaporated ata deposition rate of 0.2 nm/sec. to a thickness of about 200 nm to forma cathode, obtaining an organic EL element,

With a DC voltage applied, the EL element was continuously driven at aconstant current density of 10 mA/cm² in a dry atmosphere. At theinitial, emission of yellowish green light (maximum wavelength λmax=500nm) at a luminance of 470 cd/m² was observed with a drive voltage of 6.7V. A half life of luminance was 2,000 hours, during which the drivevoltage increased 3.0 V.

Example 27

An El element was manufactured as in Example 26 except that compound(X-10) of Example 4 was used in the hole injecting and transportinglayer and mix layer (light emitting layer) instead o compound (-1). Itwas similarly tested. The results were at least comparable to those ofExample 26.

Example 28

A glass substrate having an ITO transparent electrode (anode) of 200 mmthick was subjected to ultrasonic cleaning with neutral detergent,acetone, and ethanol. The substrate was pulled up from boiling ethanol,dried, and further subjected to UV/ozone cleaning. The substrate wassecured by a holder in an evaporation chamber, which was evacuated to avacuum of 1×10⁻⁴ Pa or lower.

First poly(thiophene-2,5-diyl) was evaporated at a deposition rate ofabout 0.1 nm/sec. to a thickness of about 20 nm, forming a first holeinjecting and transporting layer.

Then the vacuum chamber was released to the atmospheric air endevacuated again to a vacuum of 1×10⁻⁴ Pa or lower. The compound (I-1) ofExample 1 was evaporated and deposited at a rate of 0.1-0.2 nm/sec. to athickness of about 35 mm, forming a second hole injecting andtransporting layer.

With the vacuum kept, the second hole injecting and transportingmaterial and tris(8-quinolinolato)aluminum as an electron injecting andtransporting material were evaporated and co-deposited at asubstantially equal rate of 0.1-0.2 nm/sec. to form a mix layer of about40 nm thick as a light emitting layer.

With the vacuum kept, the electron injecting and transporting materialwas evaporated and deposited at a rate of 0.1-0.2 nm/sec. to a thicknessof about 30 nm, forming an electron injecting and transporting layer.

With the vacuum kept further, XgAg (weight ratio 10:1) was evaporated ata deposition rate of 0.2 nm/sec. to a thickness of about 200 nm to forma cathode, obtaining an organic EL element.

With a DC voltage applied, the EL element was continuously driven at aconstant current density of 10 mA/cm² in a dry atmosphere. At theinitial, emission of yellowish green light (maximum wavelength λmax=500nm) at a luminance of 350 cd/m² was observed with a drive voltage of 6.1V. A half life of luminance was 3,000 hours, during which the drivevoltage increased 5.0 V.

Example 29

An EL element was manufactured as in Example 28 except that the mixlayer was 10 nm thick. It was similarly tested. At the initial, emissionof yellowish green light (maximum wavelength λmax=500 nm) at a luminanceof 360 cd/m² was observed with a. drive voltage of 6.2 V. A half life ofluminance was 2,100 hours, during which the drive voltage increased 3.3V.

Example 30

An EL element was manufactured as in Example 28 except that compound(X-10) of Example 4 was used in the second hole injecting andtransporting layer and mix layer (light emitting layer) instead ofcompound (I-1). It was similarly tested. The results were at leastcomparable to those of Example 28.

Examples 9 to 30 were repeated using at least one of the illustratedexamples of the inventive compound instead of compounds (I1), (II-1),(VII-1), (X-10), and (X-3). They were similarly tested to find similarresults complying with respective element constructions.

There have been described compounds in the form of tetraaryldiaminederivatives which have a high melting point and high glass transitiontemperature and form, by evaporation, transparent smooth thin films ofquality which maintain a stable amorphous state above room temperatureover a long term. The inventive compounds can form thin films bythemselves without a need for binder resin.

The organic EL elements using organic EL element-forming compoundsincluding the inventive compounds in organic compound layers thereof,typically in a hole injecting and transporting layer thereof provideuniform plane light emission and maintain high luminance in a stablemanner over a long term. Thus the elements are fully durable andreliable.

Those EL elements including two hole injecting and transporting layers,one layer containing the inventive compound and the other layercontaining polythiophene, can operate at a reduced drive voltage with asuppressed rise thereof and without development of dark spots over along term, maintaining stable light mission. The embodiment of the ELelement designed such that the differential Ip is optimized has areduced initial drop of luminance and an extended lifetime of lightemission. Those EL elements having a rubrene doped layer are improved ininitial luminance and have an extended lifetime of light emission. ThoseEL elements having a mix layer containing the inventive compound and acompound having an electron injecting and transporting function as alight emitting layer also have an extended life of light emission.

Japanese Patent Application Nos. 014379/1994 and 145293/1994 areincorporated herein by reference.

Although some preferred embodiments have been described, manymodifications and variations may be made thereto in the light of theabove teachings. It is therefore to be understood that within the scopeof the appended claims, the invention may be practiced otherwise than asspecifically described.

What is claimed is:
 1. An organic electroluminescent element comprisingtwo electrodes and a layer between said electrodes containing at leastone organic electroluminescent element forming compound of the followingformula (2): ##STR1063## wherein A₁, A₂, A₃, and A₄, which may beidentical or different, are aryl groups attached to the correspondingbenzene ring at the para- or meta-position with respect to the positionof attachment to the nitrogen atom,R₇, R₈, R₉, and R₁₀, areindependently selected from the group consisting of an alkyl group,alkoxy group, aryl group, aryloxy group, amino group and halogen atom,r7, r8, r9, and r10 are independently 0 or an integer of 1 to 4, R₅ andR₆ are independently selected from the group consisting of an alkylgroup, alkoxy group, amino group, and halogen atom, and r5 and r6 areindependently 0 or an integer of 1 to
 4. 2. The organicelectroluminescent element of claim 1 wherein at least one of the arylgroups represented by A1 to A4 is a naphthyl, anthryl, pyrenyl,perylenyl or coronenyl group.
 3. The organic electroluminescent elementof claim 1 wherein said compound has the following formula (4):##STR1064## wherein R₇, R₈, R₉, and R₁₀ are independently selected fromthe group consisting of an alkyl group, alkoxy group, aryl group,aryloxy group, amino group and halogen atom,r7, r8, r9, and r10 areindependently 0 or an integer of 1 to 4, R₁₁, R₁₂, R₁₃, and R₁₄ areindependently selected from the group consisting of an alkyl group,alkoxy group, aryl group, aryloxy group, amino group and halogen atom,r11, r12, r13, and r14 are independently 0 or an integer of 1 to 5, R₅and R₆ are independently selected from the group consisting of an alkylgroup, alkoxy group, amino group, and halogen atom, and r5 and r6 areindependently 0 or an integer of 1 to
 4. 4. The organicelectroluminescent element of claim 3 wherein r5, r6, r7, r8, r9, r10,r11, r12, r13, and r14 are equal to
 0. 5. The organic electroluminescentelement of claim 1 wherein said compound has the following formula (5):##STR1065## wherein R₇, R₈, R₉, and R₁₀ are independently selected fromthe group consisting of an alkyl group, alkoxy group, aryl group,aryloxy group, amino group and halogen atom,r7, r8, r9, and r10 areindependently 0 or an integer of 1 to 4, R₁₁, R₁₂, R₁₃, and R₁₄ areindependently selected from the group consisting of an alkyl group,alkoxy group, aryl group, aryloxy group, amino group and halogen atom,r11, r12, r13, and r14 are independently 0 or an integer of 1 to 5, R₅and R₆ are independently selected from the group consisting of an alkylgroup, alkoxy group, amino group, and halogen atom, and r5 and r6 areindependently 0 or an integer of 1 to
 4. 6. The organicelectroluminescent element of claim 9 wherein r5, r6, r7, r8, r9, r10,r11, r12, r13, and r14 are equal to
 0. 7. The organic electroluminescentelement of claim 5, wherein at least one of R₇, R₈, R₉, and R₁₀ isdiphenylamino, bis(biphenyl)amino, N-phenyl-N-tolylamino,N-phenyl-N-biphenylamino, bis(naphthylamino), bis(anthryl)amino, orbis(pyrenyl)amino.
 8. The organic electroluminescent element of claim 1wherein said compound has the following formula (6): ##STR1066## whereinR₇, R₈, R₉, and R₁₀ are independently selected from the group consistingof an alkyl group, alkoxy group, aryl group, aryloxy group, amino groupand halogen atom,r7, r8, r9, and r10 are independently 0 or an integerof 1 to 4, R₁₁, R₁₂, R₁₃, and R₁₄ are independently selected from thegroup consisting of an alkyl group, alkoxy group, aryl group, aryloxygroup, amino group and halogen atom, r11, r12, r13, and r14 areindependently 0 or an integer of 1 to 5, R₅ and R₆ are independentlyselected from the group consisting of an alkyl group, alkoxy group,amino group, and halogen atom, and r5 and r6 are independently 0 or aninteger of 1 to
 4. 9. The organic electroluminescent element of claim 8wherein r5, r6, r7, r8, r9, r10, r11, r12, r13, and r14 are equal to 0.10. The organic electroluminescent element of claim 1 wherein saidcompound has the following formula (7): ##STR1067## wherein R₇, R₈, R₉,and R₁₀ are independently selected from the group consisting of an alkylgroup, alkoxy group, aryl group, aryloxy group, amino group and halogenatom,r7, r8, r9, and r10 are independently 0 or an integer of 1 to 4,R₁₁, R₁₂, R₁₃, and R₁₄ are independently selected from the groupconsisting of an alkyl group, alkoxy group, aryl group, aryl group,amino group and halogen atom, r11, r12, r13, and r14 are independently 0or an integer of 1 to 5, R₅ and R₆ are independently selected from thegroup consisting of an alkyl group, alkoxy group, amino group, andhalogen atom, and r5 and r6 are independently 0 or an integer of 1 to 4.11. The organic electroluminescent element of claim 10 wherein r5, r6,r7, r8, r9, r10, r11, r12, r13, and r14 are equal to
 0. 12. The organicelectroluminescent element of claim 1 wherein said compound has thefollowing formula (8): ##STR1068## wherein R₇, R₈, R₉, and R₁₀ areindependently selected from the group consisting of an alkyl group,alkoxy group, aryl group, aryloxy group, amino group and halogenatom,r7, r8, r9, and r10 are independently 0 or an integer of 1 to 4,R₁₁, R₁₂, R₁₃, and R₁₄ are independently selected from the groupconsisting of an alkyl group, alkoxy group, aryl group, aryloxy group,amino group and halogen atom, r11, r12, r13, and r14 are independently 0or an integer of 1 to 5, R₅ and R₆ are independently selected from thegroup consisting of an alkyl group, alkoxy group, amino group, andhalogen atom, and r5 and r6 are independently 0 or an integer of 1 to 4.13. The organic electroluminescent element of claim 12 wherein r5, r6,r7, r8, r9, r10, r11, r12, r13, and r14 are equal to
 0. 14. The organicelectroluminescent element of claim 1 wherein said compound has thefollowing formula (9): ##STR1069## wherein R₇, R₈, R₉, and R₁₀ areindependently selected from the group consisting of an alkyl group,alkoxy group, aryl group, aryloxy group, amino group and halogenatom,r7, r8, r9, and r10 are independently 0 or an integer of 1 to 4,R₁₁, R₁₂, R₁₃, and R₁₄ are independently selected from the groupconsisting of an alkyl group, alkoxy group, aryl group, aryloxy group,amino group and halogen atom, r11, r12, r13, and r14 are independently 0or an integer of 1 to 5, R₅ and R₆ are independently selected from thegroup consisting of an allyl group, alkoxy group, amino group, andhalogen atom, and r5 and r6 are independently 0 or an integer of 1 to 4.15. The organic electroluminescent element of claim 14 wherein r5, r6,r7, r8, r9, r10, r11, r12, r13, and r14 are equal to
 0. 16. An organicelectroluminescent element comprising two electrodes and a layer betweensaid electrodes containing at least one organic electroluminescentelement-forming compound of the following formula (3): ##STR1070##wherein Ar is an aryl group attached to the corresponding benzene ringat the para- or meta-position with respect to the position of attachmentto the nitrogen atom,Z₁, Z₂, and Z₃ are independently selected from thegroup consisting of an alkyl group, alkoxy group, aryl group, aryloxygroup, amino group and halogen atom, one or two of Z₁, Z₂, and Z₃ is anaryl group attached to the corresponding benzene ring at the para- ormeta-position with respect to the position of attachment to the nitrogenatom, with the proviso that when two of Ar, Z₁, Z₂, and Z₃ are arylgroups, at least one of Ar, Z₁, Z₂, and Z₃ is attached to thecorresponding benzene ring at the meta-position with respect to theposition of attachment to the nitrogen atom or two of Ar, Z₁, Z₂, and Z₃are diarylamino aryl groups attached to the corresponding ring at thepara-position with respect to the position of attachment to the nitrogenatom, s1, s2, and s3 are independently 0 or an integer of 1 to 5, thesum of s1, s2, and s3 is an integer of at least 1, R₀ is selected fromthe group consisting of an alkyl group, alkoxy group, aryl group,aryloxy group, amino group and halogen atom, r0 is 0 or an integer of 1to 4, R₅ and R₆ are independently selected from the group consisting ofan alkyl group, alkoxy group, amino group, and halogen atom, and r5 andr6 are independently 0 or an integer of 1 to
 4. 17. The organicelectroluminescent element of claim 16 wherein said compound has thefollowing formula (10): ##STR1071## wherein Ar₁ and Ar₂ which may beidentical or different are aryl groups,R₁₅ and R₁₆ are independentlyselected from the group consisting of an alkyl group, alkoxy group, arylgroup, aryloxy group, amino group and halogen atom, r15 and r16 areindependently 0 or an integer of 1 to 4, R₁₇ and R₁₈ are independentlyselected from the group consisting of an alkyl group, alkoxy group,aryloxy group, amino group and halogen atom, r17 and r18 areindependently 0 or an integer of 1 to 5, R₅ and R₆ are independentlyselected from the group consisting of an alkyl group, alkoxy group,amino group, and halogen atom, and r5 and r6 are independently 0 or aninteger of 1 to
 4. 18. The organic electroluminescent element of claim17 wherein r5, r6, r15, r16, r17, and r18 are equal to
 0. 19. Theorganic electroluminescent element of claim 16 wherein said compound hasthe following formula (11): ##STR1072## wherein Ar₁ and Ar₃ which may beidentical or different are aryl groups,R₁₅ and R₂₀ are independentlyselected from the group consisting of a alkyl group, alkoxy group, arylgroup, aryloxy group, amino group and halogen atom, r15 and r20 areindependently 0 or an integer of 1 to 4, R₁₈ and R₁₉ are independentlyselected from the group consisting of an alkyl group, alkoxy group,aryloxy group, amino group and halogen atom, r18 and r19 areindependently 0 or an integer of 1 to 5, R₅ and R₆ are independentlyselected from the group consisting of an alkyl group, alkoxy group,amino group, and halogen atom, and r5 and r6 are independently 0 or aninteger of 1 to
 4. 20. The organic electroluminescent element of claim19 wherein r5, r6, r15, r18, r19, and r20 are equal to
 0. 21. Theorganic electroluminescent element of claim 16 wherein said compound hasthe following formula (12): ##STR1073## wherein Ar₁, Ar₂, and Ar₃ whichmay be identical or different are aryl groups,R₁₅, R₁₆, and R₂₀ areindependently selected from the group consisting of an alkyl group,alkoxy group, aryl group, aryloxy group, amino group and halogen atom,r15, r16, and r20 are independently 0 or an integer of 1 to 4, R₁₈ isselected from the group consisting of an alkyl group, alkoxy group,aryloxy group, amino group and halogen atom, r18 is 0 or an integer of 1to 5, R₅ and R₆ are independently selected from the group consisting ofan alkyl group, alkoxy group, amino group, and halogen atom, and r5 andr6 are independently 0 or an integer of 1 to
 4. 22. The organicelectroluminescent element of claim 21 wherein r5, r6, r15, r16, r18,and r20 are equal to
 0. 23. The organic electroluminescent element ofclaim 16 wherein said compound has the following formula (13):##STR1074## wherein Ar4 and Ar₅ which may be identical or different arearyl groups,R₁₅ and R₁₆ are independently selected from the groupconsisting of an alkyl group, alkoxy group, aryl group, aryloxy group,amino group and halogen atom, r15 and r16 are independently 0 or aninteger of 1 to 4, R₁₇ and R₁₈ are independently selected from the groupconsisting of an alkyl group, alkoxy group, aryloxy group, amino groupand halogen atom, r17 and r18 are independently 0 or an integer of 1 to5, R₅ and R₆ are independently selected from the group consisting of analkyl group, alkoxy group, amino group, and halogen atom, and r5 and r6are independently 0 or an integer of 1 to
 4. 24. The organicelectroluminescent element of claim 23 wherein r5, r6, r15, r16, r17,and r18 are equal to
 0. 25. The organic electroluminescent element ofclaim 16 wherein said compound has the following formula (14):##STR1075## wherein Ar₄ and Ar₆ which may be identical or different arearyl groups,R₁₅ and R₂₀ are independently selected from the groupconsisting of an alkyl group, alkoxy group, aryl group, aryloxy group,amino group and halogen atom, r15 and r20 are independently 0 or aninteger of 1 to 4, R₁₈ and R₁₉ are independently selected from the groupconsisting of an alkyl group, alkoxy group, aryloxy group, amino groupand halogen atom, r18 and r19 are independently 0 or an integer of 1 to5, R₅ and R₆ are independently selected from the group consisting of analkyl group, alkoxy group, amino group, and halogen atom, and r5 and r6are independently 0 or an integer of 1 to
 4. 26. The organicelectroluminescent element of claim 25 wherein r5, r6, r15, r18, r19,and r20 are equal to
 0. 27. The organic electroluminescent element ofclaim 16 wherein said compound has the following formula (15):##STR1076## wherein Ar₄, Ar₅, and Ar₆ which may be identical ordifferent are aryl groups,R₁₅, R₁₆, and R₂₀ are independently selectedfrom the group consisting of an alkyl group, alkoxy group, aryl group,aryloxy group, amino group and halogen atom, r15, r16, and r20 areindependently 0 or an integer of 1 to 4, R₁₈ is selected from the groupconsisting of an alkyl group, alkoxy group, aryloxy group, amino groupand halogen atom, r18 is 0 or an integer of 1 to 5, R₅ and R₆ areindependently selected from the group consisting of an alkyl group,alkoxy group, amino group, and halogen atom, and r5 and r6 areindependently 0 or an integer of 1 to
 4. 28. The organicelectroluminescent element of claim 27 wherein r5, r6, r15, r16, r18,and r20 are equal to
 0. 29. The organic electroluminescent element ofclaim 1 or 16, additionally comprising at least one mix layer containinga mixture of the organic electroluminescent element-forming compound andat least one compound having an electron injecting and transportingfunction.
 30. The organic electroluminescent element of claim 29 whereinthe compound having an electron injecting and transporting function istris(8-quinolinolato)aluminum.
 31. The organic electroluminescentelement of claim 29 wherein said mix layer is a light emitting layer.32. The organic electroluminescent element of claim 1 or 16 wherein saidlayer containing an organic electroluminescent element-forming compoundis doped with a fluorescent material.
 33. The organic electroluminescentelement of claim 32 wherein said fluorescent material is rubrene. 34.The organic electroluminescent element of claim 1 or 16 wherein saidlayer containing an organic electroluminescent element-forming compoundis a hole injecting and transporting layer and the element furtherincludes a light emitting layer.
 35. The organic electroluminescentelement of claim 34 wherein said hole injecting and transporting layerincludes at least two layers having different compositions.
 36. Theorganic electroluminescent element of claim 35 wherein at least one ofsaid hole injecting and transporting layers contains a polythiophene.37. The organic electroluminescent element of claim 1 or 16 whichfurther includes an electron injecting and transporting layer.
 38. Theelectroluminescent element of claim 1 or 16 wherein said layercontaining an organic electroluminescent element-forming compound is alayer having a hole injecting and transporting function,a layer having alight emitting function or electron injecting and transporting functionis disposed adjacent said layer, and the difference in ionizationpotential Ip between said layer having a hole injecting and transportingfunction and said layer having a light emitting function or electroninjecting and transporting function is at least 0.25 eV.